- Synthesis and biological evaluation of chemical tools for the study of Dolichol Linked Oligosaccharide Diphosphatase (DLODP)
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Citronellyl- and solanesyl-based dolichol linked oligosaccharide (DLO) analogs were synthesized and tested along with undecaprenyl compounds for their ability to inhibit the release of [3H]OSP from [3H]DLO by mammalian liver DLO diphosphatase activity. Solanesyl (C45) and undecaprenyl (C55) compounds were 50–500 fold more potent than their citronellyl (C10)-based counterparts, indicating that the alkyl chain length is important for activity. The relative potency of the compounds within the citronellyl series was different to that of the solanesyl series with citronellyl diphosphate being 2 and 3 fold more potent than citronellyl-PP-GlcNAc2and citronellyl-PP-GlcNAc, respectively; whereas solanesyl-PP-GlcNAc and solanesyl-PP-GlcNAc2were 4 and 8 fold more potent, respectively, than solanesyl diphosphate. Undecaprenyl-PP-GlcNAc and bacterial Lipid II were 8 fold more potent than undecaprenyl diphosphate at inhibiting the DLODP assay. Therefore, at least for the more hydrophobic compounds, diphosphodiesters are more potent inhibitors of the DLODP assay than diphosphomonoesters. These results suggest that DLO rather than dolichyl diphosphate might be a preferred substrate for the DLODP activity.
- Bosco, Micha?l,Massarweh, Ahmad,Iatmanen-Harbi, Soria,Bouhss, Ahmed,Chantret, Isabelle,Busca, Patricia,Moore, Stuart E.H.,Gravier-Pelletier, Christine
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p. 952 - 964
(2016/10/25)
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- Structure-Odor Activity Studies on Monoterpenoid Mercaptans Synthesized by Changing the Structural Motifs of the Key Food Odorant 1-p-Menthene-8-thiol
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1-p-Menthene-8-thiol (1) has been discovered as the key odorant in grapefruit juice several decades ago and contributes to the overall odor of the fruit with an extremely low odor threshold of 0.000034 ng/L in air. This value is among the lowest odor thresholds ever reported for a food odorant. To check whether modifications in the structure of 1 would lead to changes in odor threshold and odor quality, 34 mercapto-containing p-menthane and 1-p-menthene derivatives as well as several aromatic and open-chain mercapto monoterpenoids were synthesized. Eighteen of them are reported for the first time in the literature, and their odor thresholds and odor qualities as well as analytical data are supplied. A comparison of the sensory data with those of 1 showed that hydrogenation of the double bond led to a clear increase in the odor threshold. Furthermore, moving the mercapto group into the ring always resulted in higher odor thresholds compared to thiols with a mercapto group in the side chains. Although all tertiary thiols always exhibited low odor thresholds, none of the 31 compounds reached the extremely low threshold of 1. Also, none of the synthesized mercapto monoterpenoids showed a similar odor quality resembling grapefruit. Although the saturated and aromatic analogues exhibited similar scents as 1, the aromas of the majority of the other compounds were described as sulfury, rubber-like, burned, soapy, or even mushroom-like. NMR and MS data as well as retention indices of the 23 newly reported sulfur-containing compounds might aid in future research to identify terpene-derived mercaptans possibly present in trace levels in foods.
- Schoenauer, Sebastian,Schieberle, Peter
-
p. 3849 - 3861
(2016/06/01)
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- Pheromone synthesis. Part 256: Synthesis of the four stereoisomers of 5,11-dimethylpentacosane, a new sex pheromone component of the male Galleria mellonella (L.), with high stereochemical purities as determined by the derivatization-HPLC analysis of the eight stereoisomers of 5,11-dimethyl-8-pentacosanol
-
Abstract All the four stereoisomers of 5,11-dimethylpentacosane (>96.8% purity) were synthesized via the stereoisomers of 5,11-dimethyl-8-pentacosanol, whose stereoisomeric compositions could be determined precisely by their low temperature HPLC analysis after derivatization. 5,11-Dimethyl-8-pentacosanol was prepared by a Grignard reaction between 3-methylheptylmagnesium bromide and 4-methyloctadecanal, both of which were prepared from the commercially available enantiomers of citronellal (97-98% ee). Alternatively, (R)-3-methyl-1-heptanol could be prepared from methyl (R)-3-hydroxybutanoate (100% ee). Pd/C-catalyzed hydrogenation of a 5-methyl-1-alkene caused partial racemaization at C-5.
- Mori, Kenji,Akasaka, Kazuaki
-
p. 4102 - 4115
(2015/06/02)
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- PRODUCTION METHOD OF 4,8-DIMETHYLDECANAL
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PROBLEM TO BE SOLVED: To provide a method of producing a mixture of (4R,8S)-4,8-dimethyldecanal and (4R,8R)-4,8-dimethyldecanal effective as pheromones for rust-red flour beetles and confused flour beetles, practically in a high yield through a small number of steps. SOLUTION: A method of producing a mixture of (4R,8S)-4,8-dimethyldecanal and (4R,8R)-4,8-dimethyldecanal includes a first step of tosylating (S)-citronellol to obtain a tosylate, a second step of reacting the tosylate with a Grignard reagent to obtain an alkene, a third step of epoxidating the alkene to obtain an epoxide, and a fourth step of cleaving the epoxide with a periodic acid to obtain 4,8-dimethyldecanal. COPYRIGHT: (C)2015,JPOandINPIT
- -
-
Paragraph 0009; 0012; 0018
(2016/12/12)
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- Synthesis of all the stereoisomers of 6-methyl-2-octadecanone, 14-methyl-2-octadecanone, and 6,14-dimethyl-2-octadecanone, sex pheromone components of the Lyclene dharma dharma moth, from the enantiomers of citronellal
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The enantiomers of citronellal were converted to all the stereoisomers of 6-methyl-2-octadecanone, 14-methyl-2-octadecanone, and 6,14-dimethyl-2- octadecanone, the female-produced sex pheromone components of the Lyclene dharma dharma moth. Three wellestablished procedures, the Wittig reaction, alkylation of alkynes, and acetoacetic ester synthesis, were employed for the carbon-carbon bond formation to connect the building blocks.
- Shikichi, Yasumasa,Mori, Kenji
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p. 1943 - 1951
(2013/01/15)
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- Total synthesis of a cuticular hydrocarbon from the cane beetle Antitrogus parvulus: Confirmation of the relative stereochemistry
-
The stereoselective reaction of an allyl bromide with an aldehyde mediated by a low valency bismuth species was the key reaction in stereoselective syntheses of (4S,6R,8R,10S,16S)- and (4S,6R,8R,10S,16R)-4,6,8,10,16- pentamethyldocosanes. 13C N
- Basar, Norazah B.,Liu, Hao,Negi, Devendra,Sirat, Hasnah M.,Morris, Gareth A.,Thomas, Eric J.
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supporting information; experimental part
p. 1743 - 1745
(2012/04/23)
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- Aliphatic C-H to C-C conversion: Synthesis of (-)-cameroonan-7α-ol
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In the course of a synthesis of the tricyclic sesquiterpene (-)- cameroonan-7α-ol from the acyclic (〈)-citronellal, seven aliphatic C-H bonds were converted to C-C bonds, and three rings and four new stereogenic centers were established. 2011 American Chemical Society.
- Taber, Douglass F.,Nelson, Christopher G.
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p. 1874 - 1882
(2011/06/23)
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- Liposomal circular dichroism. assignment of remote stereocenters in plakinic acids K and L from a plakortis-xestospongia sponge association
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"Figure Presented" Two new ωtu-phenyl polyketide peroxides, plakinic acids K and L, were isolated from a two-sponge association of Plakortis halichondroides and Xestospongia deweerdtae. The absolute configurations of the remote dimethyl-branched stereocenters in plakinic acid K were assigned by degradation of plakinic acid K to a long-chain naphthamide and analysis by liposomal circular dichroism (L-CD) and comparison with synthetic standards.
- Dalisay, Doralyn S.,Quach, Tim,Molinski, Tadeusz F.
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scheme or table
p. 1524 - 1527
(2010/06/20)
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- Composition of the cloacal gland secretion of tuatara, Sphenodon punctatus
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The lipophilic content of the cloacal gland secretion of the tuatara (Sphenodon punctatus) was investigated. GC/EI-MS Analysis of CH2Cl2 extracts of the secretions revealed triacylglycerols as major glandular constituents. Twelve major medium-chain fatty acids were found to be conjugated to glycerol in different combinations, resulting in complex mixtures. These acids were identified by transesterification and subsequent derivatization of natural samples, and their structures were verified by synthesis. The natural glycerides contain predominantly three of the following acids: octanoic (A), (E)- and (Z)-oct-4-enoic (B and C, resp.), (4E,6Z)-octa-4,6-dienoic (tuataric acid;D), (R)-2,6-dimethylheptanoic (E), (R)-2,6-dimethylhept-5-enoic (F), (Z)-dec-4-enoic (G), (4Z,7Z)-deca-4,7-dienoic (H), (R)-3,7-dimethyloct-6-enoic (I), (R)-4,8-dimethylnon-7-enoic (J), (2R,6S)-2,6,10-trimethylundec-9-enoic (K), and (2R,5E)-2,6,10-trimethylundeca-5,9-dienoic acids (L). Several additional acids, occurring in trace amounts only, were tentatively identified by MS. The elucidation of the absolute configuration of the acids was performed by GC on chiral phases. Individual tuatara show specific mixtures of glycerides with up to 100 components. The individual mixtures may permit individual recognition because the bouquets seem to be stable over years.
- Flachsbarth, Birte,Fritzsche, Matthias,Weldon, Paul J.,Schulz, Stefan
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experimental part
p. 1 - 37
(2010/04/23)
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- Synthesis of all the six components of the female-produced contact sex pheromone of the German cockroach, Blattella germanica (L.)
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All of the following six components of the female sex pheromone of the German cockroach, Blattella germanica (L.) were synthesized: (3S,11S)-3,11-dimethyl-2-nonacosanone (1), its 29-hydroxy derivative 2, its 29-oxo derivative 3, (3S,11S)-3,11-dimethyl-2-heptacosanone (4), its 27-hydroxy derivative 5, and its 27-oxo derivative 6. Both the enantiomers of citronellal were employed as the chiral sources and Wacker oxidation was employed for the introduction of the carbonyl group at C-2.
- Mori, Kenji
-
p. 4060 - 4071
(2008/09/20)
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- Synthesis and structure of phosphatidylinositol dimannoside
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(Chemical Equation Presented) (R)-Tuberculostearic acid (2) was synthesized in seven steps from (S)-citronellol (5). The carbon chain of 2 was assembled by copper-catalyzed cross coupling of (5)-citronellol tosylate (6) and hexylmagnesium bromide; subsequent ozonolysis and reaction with 6-benzyloxyhexylmagnesium bromide furnished alcohol 10. Functional group manipulation afforded (R)-2 in 49% overall yield from 5. DCC coupling of (R)-2 with 3-O-benzyl-1-O-palmitoyl-sn-glycerol (16), followed by hydrogenolytic removal of the benzyl group and treatment with benzyl bis(diisopropyl) phosphoramidite, afforded phosphoramidite 20. Tetrazole-mediated coupling of 20 with PIM1 head group 21 gave 22, and subsequent debenzylation afforded phosphatidylinositol mono-mannoside, PIM1 (23). Similarly, coupling of 20 and 24 and removal of the benzyl protecting groups gave PIM2 (1c). Both 23 and 1c have a clearly defined acylation pattern, which was confirmed by mass spectrometry, with sn-1 palmitoyl and sn-2 tuberculostearoyl groups on the glycerol moiety. Both 23 and 1c were shown to modulate the release of the pro-inflammatory cytokine, IL-12, in a dendritic cell assay.
- Dyer, Blake S.,Jones, Jeremy D.,Ainge, Gary D.,Denis, Michel,Larsen, David S.,Painter, Gavin F.
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p. 3282 - 3288
(2008/02/04)
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- Total synthesis of papulacandin D
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A total synthesis of the antifungal agent papulacandin D is reported. The molecule is representative of a large class of C-aryl glycosides that exhibit significant antifungal activity. The synthetic strategy bifurcates the molecule into two nearly equal subunits, the arylglycoside and 18-carbon fatty acid side chain. The key strategic transformations are (1) the palladium catalyzed, organosilanolate-based cross-coupling of a protected glucal silanol and (2) a catalytic enantioselective allylation of a dienal using allyltrichlorosilane. The synthesis was accomplished in 31 steps overall from commercial starting materials to afford over 50 mg of the natural product. Copyright
- Denmark, Scott E.,Regens, Christopher S.,Kobayashi, Tetsuya
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p. 2774 - 2776
(2008/02/02)
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- Synthesis of (4R,8R)- and (4S,8R)-4,8-dimethyldecanal: the common aggregation pheromone of flour beetles
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The synthesis of (4R,8R)- and (4S,8R)-4,8-dimethyldecanal 1 and 1a has been achieved connecting the chiral building block (R)-2-methyl-1-bromobutane 4 with (R)- and (S)-citronellol derivatives. The key intermediate 4 was obtained optically pure in five steps from methyl (S)-3-hydroxy-2-methylpropionate 2.
- Santangelo, Ellen M.,Corrêa, Arlene G.,Zarbin, Paulo H.G.
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p. 5135 - 5137
(2007/10/03)
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- Synthesis of the four stereoisomers of 7-acetoxy-15-methylnonacosane, a component of the female sex pheromone of the screwworm fly, Cochliomyia hominivorax
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The four stereoisomers of 7-acetoxy-15-methylnonacosane (1), a component of the female sex pheromone of the New World screwworm fly (Cochliomyia hominivorax) were synthesized. The stereogenic center at C-15 of 1 originated from that of the enantiomers of citronellal, and that at C-7 was generated by lipase-catalyzed asymmetric acetylation of (3RS,11R)- and (3RS,11S)-17-methyl-1- trimethylsilylpentacos-1-yn-3-ol (13). Three of the stereoisomers of 1 showed equivalent good pheromone activity, while the activity of (7R,15R)-1 was weak.
- Mori, Kenji,Ohtaki, Takashi,Ohrui, Hiroshi,Berkebile, Dennis R.,Carlson, David A.
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p. 1768 - 1778
(2007/10/03)
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- Synthesis of the enantiomers of some methyl-branched cuticular hydrocarbons of the ant, Diacamma sp.
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The enantiomers of 3-methylpentacosane, 3-methylheptacosane, 3-methylnonacosane, 13-methylheptacosane, and 5-methylheptacosane were synthesized by starting from the enantiomers of 2-methylbutyl bromide or citronellol. These methyl-branched alkanes are the characteristic components of the cuticular hydrocarbons of queen of the ant, Diacamma sp.
- Marukawa, Kaoru,Takikawa, Hirosato,Mori, Kenji
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p. 305 - 314
(2007/10/03)
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- Absolute Configuration of a Ceramide with a Novel Branched-chain Fatty Acid Isolated from the Epiphytic Dinoflagellate, Coolia monotis
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The absolute configuration of the chiral center at the C15 position of a novel branched-chain fatty acid derived from a new ceramide isolated from the epiphytic dinoflagellate Coolia monotis was determined to be of R from by reversed-phase HPLC after clea
- Akasaka, Kazuaki,Shichijyukari, Seiya,Matsuoka, Shigeru,Murata, Michio,Meguro, Hiroshi,Ohrui, Hiroshi
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p. 1842 - 1846
(2007/10/03)
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- Synthesis of the spiroacetal parts of spirofungin A and B
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The C9-C20 spiroacetal parts of spirofungin A and B, antifungal antibiotics from Streptomyces violaceusniger Tu 4113, were synthesized simultaneously from (S)-citronellyl bromide and (±)-epoxy alcohol via alkyne-lactone coupling reaction and diastereomeric separation. (C) 2000 Elsevier Science Ltd.
- Shimizu, Yuko,Kiyota, Hiromasa,Oritani, Takayuki
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p. 3141 - 3144
(2007/10/03)
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- Pheromone synthesis, CXCIX([≠]). Synthesis of all the stereoisomers of 7-methylheptadecane and 7,11-dimethylheptadecane, the female sex pheromone components of the spring hemlock looper and the pitch pine looper
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All the stereoisomers of 7-methylheptadecane (1) and 7,11- dimethylheptadecane (2) were synthesized by starting from the enantiomers of citronellol (3) and methyl 3-hydroxy-2-methylpropanonate (8), respectively. A short synthesis of meso-7,11-dimethylheptadecane [(7R, 11S)-2] was achieved starting from meso-2,6-dimethylheptanedioic acid [(2R,6S)21]. A mixture of (S)-1 and (7R, 11S)-2 is the pheromone of the spring hemlock looper moth (Lambdina athasaria) and the pitch pine looper moth (L. pellucidaria).
- Shirai, Yasuo,Seki, Masanori,Mori, Kenji
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p. 3139 - 3145
(2007/10/03)
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- Pheromone synthesis, CXCIV. - Synthesis of the enantiomers of (Z)-21- methyl-8-pentatriacontene, the major component of the female-produced contact sex pheromone of the yellow-spotted longicorn beetle, Psacothea hilaris
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Both the enantiomers of (Z)-21-methyl-8-pentatriacontene (1), the major component of the female-produced contact sex pheromone of the yellow-spotted longicorn beetle (Psacothea hilaris), were synthesized by starting from the enantiomers of citronellol (2).
- Domon, Kenji,Takikawa, Hirosato,Mori, Kenji
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p. 981 - 984
(2007/10/03)
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- Pheromone synthesis, CLXXIV: Synthesis of (5R,11S)-5,11-Dimethylheptadecane and (S)-2,5-Dimethylheptadecane, the major and the minor components of the sex pheromone of the geometrid moth, Lambdina fiscellaria lugubrosa
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(5R,11S)-5,11-Dimethylheptadecane (1), the major component of the female-produced sex pheromone of the western hemlock looper (Lambdina fiscellaria lugubrosa), was synthesized by starting from the enantiomers of methyl 3-hydroxy-2-methylpropanoate (3). (S)-2,5-Dimethylheptadecane (2), the minor and synergistic component of the pheromone, was also synthesized by starting from (S)-citronellol (4). VCH Verlagsgesellschaft mbH, 1996.
- Mori, Kenji,Horikiri, Hiromasa
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p. 501 - 505
(2007/10/03)
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- Pheromone Synthesis, CLXXVI: Synthesis of the four stereoisomers of 3,13-dimethylheptadecane, the major sex pheromone component of the western false hemlock looper
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All of the four stereoisomers of 3,13-dimethylheptadecane (1), the female-produced sex pheromone of the western false hemlock looper (Nepytia freemani), were synthesized by starting from the enantiomers of citronellol (2a) and 2-methyl-1-butanol (4a). VCH Verlagsgesellschaft mbH, 1996.
- Takikawa, Hirosato,Shirai, Yasuo,Kobayashi, Makoto,Mori, Kenji
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p. 1965 - 1970
(2007/10/03)
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- Pheromone Synthesis, CXLIX. Synthesis of (2E,4E,6R,10S)-4,6,10-Trimethyl-2,4-dodecadien-7-one - the Major Component of the Sex Pheromone of the Maritime Pine Scale (Matsucoccus feytaudi) - and its Three Stereoisomers
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(2E,4E,6R,10S)-4,6,10-Trimethyl-2,4-dodecadien-7-one (1) - the major component of the sex pheromone of the maritime pine scale - and its three stereoisomers were synthesized by starting from (R)- or (S)-citronellol (4) and employing the asymmetric epoxidation (9 -> 10) and the palladium-catalyzed reductive cleavage of the epoxy ring (13 -> 14) as the key steps.Key Words: Asymmetric epoxidation / 2,4-Dodecadien-7-one, 4,6,10-trimethyl / Maritime pine scale / Matsucoccus feytaudi / Pheromones
- Mori, Kenji,Harashima, Susumu
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p. 391 - 402
(2007/10/02)
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- Synthesis of (2E,4E,6R,10R)-4,6,10,12-Tetramethyl-2,4-tridecadien-7-one (Matsuone) - the Primary Component of the Sex Pheromone of Three Matsucoccus Pine Bast Scales - and Its Antipode
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(2E,4E,6R,10R)-4,6,10,12-Tetramethyl-2,4-tridecadien-7-one (1; matsuone) - the primary component of the sex pheromone of the red pine scale (Matsucoccus resinosae) and two other pine scales - and its antipode were synthesized by starting from (R)- or (S)-
- Mori, Kenji,Harashima, Susumu
-
p. 993 - 1002
(2007/10/02)
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- OZONOLYSIS OF ALKENES AND REACTIONS OF POLYFUNCTIONAL COMPOUNDS. XLVI. SYNTHESIS OF (4S,8S)-4,8-DIMETHYLDECANAL AND ITS DIMETHYL ACETAL
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From accessible chiral structural blocks, namely, (R)-methyl-citronellate and (S)-2-methyl-1-butanol, (6S,10S)-2,6,10-trimethyl-2-dodecene was synthesized.The ozonolysis of this gave (4S,8S)-4,8-dimethyldecanal, one of the stereoisomers of the aggregation pheromone of the meal worms Tribolium confusium and T. castaneum, and its dimethyl acetal.
- Odinokov, V. N.,Akhmetova, V. R.,Khasanov, Kh. D.,Abduvakhabov, A. A.,Sul'tanmuratova, V. R.,Tolsikov, G. A.
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p. 915 - 918
(2007/10/02)
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- Assignment of (6R*10R*)-relative stereochemistry to the major component of the sex pheromone of the maritime pine scale, Matsucoccus feytaudi
-
(2E,4E,6R,10S)-4,6,10-Trimethyl-2,4-dodecadien-7-one 1 and its (6S,10S)-isomer were synthesized. The 1H NMR spectrum of (6S,10S)-1 coincided with that reported for the major component of the sex pheromone of Matsucoccus feytaudi, which must therefore be either (6S,10S)- or (6R,10R)-1.
- Mori,Harashima
-
p. 5995 - 5998
(2007/10/02)
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- Biosynthesic Studies of Marine Lipids. 11. Synthesis, Biosynthesis, and Absolute Configuration of the Internally Branched Demospongic Acid, 22-Methyl-5,9-octacosadienoic Acid
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The 14C-labeled short-chain fatty acid 10-methylhexadecanoic acid (10-Me-16:0) as well as its hitherto undescribed 10R and 10S antipodes was incorporated into the marine sponge Aplysina fistularis and transformed in situ into 22-methyl-5,9-octacosadienoic acid (22-Me-Δ5,9-28:2) by chain elongation.No qualitative specificity between the two enantiomers was observed. Methionine was also incorporated into the sponge to investigate the methylation process; a rapid incorporation into the short branched fatty acids occurred with subsequent chain elongation.Both enantiomers were synthesized starting from (+)-pulegone to determine the absolute configuration of the 22-methyl-5,9-octacosadienoic (22-Me-Δ5,9-28:2) acid.The naturally occurring acid has the 22R configuration.
- Raederstorff, Daniel,Shu, Arthur Y.L.,Thompson, Janice E.,Djerassi, Carl
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p. 2337 - 2346
(2007/10/02)
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- Syntheses of the Sex-Attractant of Pine Sawfies
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In order to establish the stereochemistry of the sex attractant of various species of pine sawflies, (2S,3R,7R)-, (2S,3R,7S)- and (2S,3S,7S)-2-acetoxy- and 2-propionyloxy-3,7-dimethylpentadecane were synthesized.The alcohol moiety of each pheromone was prepared by the coupling of Grignard reagent of C12 block with tosylate of C5 block.The C12 block, (R)- and (S)-1-bromo-2-methylundecane, were prepared from (R)-(+)-pulegone.The C5 block, (2R,3S)- or (2S,3S)-2-methyl-3-tetrahydropyranyloxy-1-(tosyloxy)butane, were derived from (2S,3S)- or (2R,3S)-2-methyl-3-hydroxy butyric acid prepared by the enantio-differentiating hydrogenation of methyl 2-methyl-3-oxobutyrate over the asymmetrically modified nickel catalyst.
- Kikukawa, Tadashi,Imaida, Motomasa,Tai, Akira
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p. 1954 - 1960
(2007/10/02)
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- SYNTHESIS OF THE SEX-ATTRACTANT OF PINE SAWFLIES (DIPRION SPECIES); (2S,3R,7R)- AND (2S,3R,7S)-3,7-DIMETHYLPENTADECAN-2-Ol
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In order to establish the stereochemistry of the sex attractant of diprion species of pine sawflies, two candidate epimers, (2S,3R,7R)- and (2S,3R,7S)-3,7-dimethylpentadecan-2-ol were synthesized by the coupling reaction of optically active C5 and C12 units.The C12 units, (R)-(-)- and (S)-(+)-1-bromo-2-methylundecane were prepared from (R)-(+)-pulegone.The C5 unit, (2R,3S)-2-methyl-3-tetrahydropyranoxy-1-tosyloxybutane was derived from (2S,3S)-2-methyl-3-hydroxybutyric acid prepared by the reported procedure.
- Kikukawa, Tadashi,Imaida, Motomasa,Tai, Akira
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p. 1799 - 1802
(2007/10/02)
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- Synthese von optisch aktiven Trogoderma-Pheromonen durch Kolbe-Elektrolyse
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The (R)-(-)-enantiomers of (Z)- (1) and (E)-14-methyl-8-hexadecen-1-ol (2) have been synthesized by coelectrolysis of (R)-(-)-4-methylhexanoic acid (7) with 12-(tetrahydro-2-pyranyloxy)-4-dodecynoic acid (8) and its subsequent hydrogenation.The acid 7 was prepared in high optical purity from (S)-(-)-citronellol (3) by conversion of the hydroxyl group to a methyl substituent and subsequent cleavage of (R)-(-)-2,6-dimethyl-2-octene (4) with ozone.By alkylation of 4-pentynoic acid (5) with 1-bromo-7-(tetrahydro-2-pyranyloxy)heptane (6) the alkynoic acid 8 was synthesized.
- Jensen, Uta,Schaefer, Hans-J.
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p. 292 - 297
(2007/10/02)
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