- Total synthesis of leukotrienes from butadiene
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The total synthesis of leukotrienes has been achieved starting from butadiene by a palladium-catalyzed telomerization at room temperature. A Sharpless catalytic asymmetric epoxidation generated the asymmetric centers with >94% ee. Simple transformations of the key intermediate 15 produced the leukotrienes LTA4 methyl ester (4), LTC4 (1), LTD4 (2) and LTE4 (3), as well as (14S, 15S)-LTA4 methyl ester (24) and the novel [2H2]-LTA4 methyl ester (28). The use of the opposite chiral director in the Sharpless catalytic asymmetric epoxidation gave the key intermediate 15a that has been used in the synthesis of the double epimers of the leukotrienes as well as LTB4.
- Rodriguez, Ana,Nomen, Miguel,Spur, Bernd W.,Godfroid, Jean-Jacques,Lee, Tak H.
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p. 2991 - 3000
(2007/10/03)
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- A FACILE STEREOSELECTIVE SYNTHESIS OF LEUKOTRIENE A4(LTA4) METHYL ESTER
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A facile synthesis of LTA4 1 methyl ester was achieved according to Scheme 1, in which the key intermediate 6 and 7 were prepared with the new procedures conveniently, stereoselectively and in good yields.
- Wang, Yanfang,Li, Jincui,Wu, Yulin,Huang, Yaozeng,Shi, Lilan,Yang, Jianhua
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p. 4583 - 4584
(2007/10/02)
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- Oxidized Leukotrienes: Synthesis of 20-OH and 20-COOH LTD4. Possible Metabolites in the Lipoxygenase Pathway
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Leukotriene LTD4 analogs 20-OH LTD4 16 and 20-COOH LTD4 17 were synthesized.These ω-oxidative derivatives are possible metabolites of the natural product.
- Adams, Julian,Milette, Suzanne,Rokach, Joshua,Zamboni, Robert
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p. 2179 - 2182
(2007/10/02)
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- Enantiospecific syntheses of leukotrienes C4, D4 and E4 and [14,15-3H2]leukotriene E4 dimethyl ester
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A 'chiral-pool' approach was employed to synthesize various leukotrienes (slow-reacting substance of anaphylaxis, SRS-A) enantiospecifically. The pivotal (S,S)-trans-epoxy alcohol 9 was prepared by efficient and facile routes starting from erythorbic acid (D-araboascorbic acid, 13). This epoxide could also be produced starting from D-glucose. The epimeric (S,R)-cis-epoxide 38 was obtained utilizing L-tartaric acid as the chiral starting material. Elaboration of 9 into leukotriene A4 methyl ester (5) and the potassium salts of leukotrienes C4 (4a), D4 (4b), and E4 (4c) was accomplished by standard methods. These salts exhibited potent contractile activities in the in vitro guinea pig ileum assay. Reduction of 14,15-dehydroleukotriene A4 methyl ester (44) with tritium gas gave [14,15-3H2]-5 and subsequently the dimethyl ester of [14,15-3H2]leukotriene E4 having a high specific activity of 40 Ci/mmol.
- Cohen,Banner,Lopresti,et al.
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p. 3661 - 3672
(2007/10/02)
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- SYNTHESIS OF THE 7-CIS ISOMER OF THE NATURAL LEUKOTRIENE D4
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Methyl 5(S),6(S)-oxido-11-oxo-7-cis-9-trans-undecadienoate 5 was prepared and used for the synthesis of the novel 7-cis-LTD4 (9) as well as, after isomerization to the all-trans dienal ester 3, for that of the natural leukotrienes.
- Ernest, I.,Main, A. J.,Menasse, R.
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p. 167 - 170
(2007/10/02)
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- SYNTHESIS OF LEUKOTRIENES - NEW SYNTHESIS OF NATURAL LEUKOTRIENE A4
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The acetonides of D- or L-glyceraldehyde are chiral synthons for an efficient and versatile synthesis of the natural leukotrienes A4, C4, D4 and E4 and equally can be used to prepare the corresponding unnatural analogues.
- Rokach, Joshua,Young, Robert N.,Kakushima, Masatoshi,Lau, Cheuk-Kun,Seguin, Rick,at al.
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p. 979 - 982
(2007/10/02)
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- THE STEREOSPECIFIC SYNTHESIS OF LEUKOTRIENE A4 (LTA4), 5-EPI-LTA4, 6-EPI-LTA4 AND 5-EPI,6-EPI-LTA4
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The stereospecific synthesis of the four isomers of 6-formyl-5,6-epoxy hexanoic acid methyl ester 8, 15, 23, 30 from 2-deoxy-D-ribose have allowed the preperation of methyl esters of LTA4, 1, and its three unnatural isomers.
- Rokach, Joshua,Zamboni, Robert,Lau, Cheuk-Kun,Guindon, Yvan
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p. 2759 - 2762
(2007/10/02)
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