Letters
J ournal of Medicinal Chemistry, 2004, Vol. 47, No. 2 295
C.; Martin, T.; Martin, V. S. â-Hydroxy-γ-lactones as chiral
building blocks for the enantioselective synthesis of marine
natural products. J . Org. Chem. 2001, 66, 1420-1428.
(12) Ragoussis, N. Modified Knoevenagel condensations. Synthesis
of (E)-3-alkenoic acids. Tetrahedron Lett. 1987, 28, 93-96.
(13) Vohra, S. K.; Harrington, G. W.; Swer, D. Reversible intercon-
version of N-nitroso(2-methylamino)acetonitrile and 3-methyl-
5-amino-1,2,3-oxadiazolium chloride and related reactions. J .
Org. Chem. 1978, 43, 1671-1673.
(14) Gao, Y.; Klunder, J . M.; Hanson, R. M.; Masamune, H.; Ko, S.
Y.; Sharpless, K. B. Catalytic Asymmetric Epoxidation and
Kinetic Resolution: Modified Procedures Including in situ
Derivatization. J . Am. Chem. Soc. 1987, 109, 5765-5780.
(15) Yadav, J . S.; Maiti, A. Asymmetric total syntheses of panaxytriol
and panaxydol, potent antitumor agents from Panax ginseng.
Tetrahedron 2002, 58, 4955-4961.
Refer en ces
(1) Goetzl, E. J .; An, S.; Smith, W. L. Specificity of expression and
effects of eicosanoid mediators in normal physiology and human
diseases. FASEB. J . 1995, 9, 1051-1058.
(2) Phipps, R. P.; Stein, S. H.; Roper, R. L.
A new view of
prostaglandin-E regulation of the immune response. Immunol.
Today 1991, 12, 349-352.
(3) Chulada, P. C.; Thompson, M. B.; Mahler, J . F.; Doyle, C. M.;
Gaul, B. W.; Lee, C.; Tiano, H. F.; Morham, S. G.; Smithies, O.;
Langenbach, R. Genetic disruption of Ptgs-1, as well as Ptgs-2,
reduces intestinal tumorigenesis in Min mice. Cancer Res. 2000,
60, 4705-4708.
(4) Sumitani, K.; Kamijo, R.; Toyoshima, T.; Nakanishi, Y.; Tak-
izawa, K.; Hatori, M.; Nagumo, M. Specific inhibition of cy-
clooxygenase-2 results in inhibition of proliferation of oral cancer
cell lines via suppression of prostaglandin E2 production. J . Oral
Pathol. Med. 2001, 30, 41-47.
(5) Gately, S. The contributions of cyclooxygenase-2 to tumor
angiogenesis. Cancer Metastasis Rev. 2000, 19, 19-27.
(6) Tsuda, T.; Fukumoto Y.; Hamamori Y.; Yamashita, T.; Takai,
Y. Involvement of two intracellular messenger systems, protein
(16) Clode, D. M. Carbohydrate cyclic acetal formation and migration.
Chem. Rev. 1979, 79, 491-513.
(17) Hanessian, S.; Lavalle, P. Preparation and synthetic utility of
tert-butyldiphenylsilyl ethers. Can. J . Chem. 1975, 53, 2975-
2977.
kinase
C
and cyclic AMP, in the regulation of c-fos gene
(18) Evans, E. H.; Hewson, A. T.; March, L. A.; Nowell, I. W. The
acid-catalyzed cyclization of methyl 1-(3-oxobutyl)-2-oxocyclo-
pentanecarboxylate X-ray-analysis of the product. J . Chem. Soc.,
Chem. Commun. 1982, 23, 1342-1343.
(19) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Catalytic
Asymmetric Dihydroxylation. Chem. Rev. 1994, 94, 2483-2547.
(20) Breyer, R. M.; Bagdassarian, C. K.; Myers, S. A.; Breyer, M. D.
Prostanoid receptors: subtypes and signaling. Annu. Rev. Phar-
macol. Toxicol. 2001, 41, 661-690.
(21) Danesch, U.; Weber, P. C.; Sellmayer, A. Arachidonic acid
increase c-fos and Egr-1 mRNA in 3T3 fibroblasts by formation
of prostaglandin E2 and activation of protein kinase C. J . Biol.
Chem. 1994, 269, 27258-27263.
(22) Danesch U.; Weber P. C.; Sellmayer, A. Differential effects of
n-6 and n-3 polyunsaturated fatty acids on cell growth and early
gene expression in Swiss 3T3 fibroblasts. J . Cell Physiol. 1996,
168, 618-624.
(23) Herschman, H. R. Primary response genes induced by growth
factors and tumor promoters. Annu. Rev. Biochem. 1991, 60,
281-319.
(24) J iang, H.; Lin, J .; Su, Z. Z.; Collart, F. R.; Huberman, E.; Fisher,
P. B. Induction of differentiation in human promyelocytic HL-
60 leukemia cells activates p21, WAF1/CIP1 expression in the
absence of p53. Oncogene 1994, 9, 3397-3406.
(25) Dertinger, S. D.; Torous, D. K.; Tometsko, A. M. Modulation of
phorbol ester-induced HL-60 differentiation by prostaglandin E2.
Mut. Res. 1995, 328, 55-62.
(26) Ishiguro, S.; Takahashi, N.; Nemoto, K.; Negishi, M.; Ichikawa,
A. Potentiation of retinoic acid-induced differentiation of HL-
60 cells by prostaglandin EP2 receptor. Prostaglandins Other
Lipid Mediat. 1998, 56, 145-153.
expression in human promyelocytic leukemia (HL-60) cells. J .
Biochem. (Tokyo) 1987, 102, 1579-1583.
(7) Fitzgerald, J .; Dietz, T. J .; Hughes-Fulford, M. Prostaglandin
E2 induced up-regulation of c-fos messenger ribonucleic acid is
primarily mediated by 3’,5’-cyclic adenosine monophosphate in
MC3T3-E1 osteoblasts. Endocrinology 2000, 141, 291-298.
(8) (a) Ballini, R.; Marcatoni, E.; Petrini, M. Enantioselective
synthesis of the lactone moiety of the mevinic acids using
D-xylose as a chiral precursor. J . Chem. Soc., Perkin Trans. 1.
1991, 2, 490-491. (b) Kabeya, M.; Hamada, Y.; Shioiri, T.
Synthesis of γ-lactone derivatives as a key intermediate for the
spiroketal fragment in calyculin A. Tetrahedron. 1997, 53, 9769-
9776. (c) Okabe, M.; Sun, R. C.; Zenchoff, G. B. Synthesis of
1-(2,3-dideoxy-2-fluoro-beta-D-threo-pentofuranosyl)cytosine
(F-ddC) - a promising agent for the treatment of acquired-
immune-deficiency-syndrome. J . Org. Chem. 1991, 56, 4392-
4397.
(9) (a) Matsumoto, K.; Ebata, T.; Koseki, K.; Okano, K.; Kawahami,
H.; Matsushita, H. Short synthesis of (3S,4R)-3-hydroxy-4-
hydroxymethyl-1,4-butanolides, two lactones from levoglucose-
none. Bull. Chem. Soc. 1995, 68, 670-672. (b) Takashi, T.; Kiwa,
T. Preparation of optically active 4-hydroxymethyl-3-(3-hydroxy-
1-propenyl)-4-butanolide derivatives as intermediates for pros-
taglandins. J pn Kokai J P. Patent 03005470 A2 19910111, 1991.
(c) Katsuya, M.; Takashi, E.; Koshi, K.; Koji, O.; Hiroshi, K.;
Hajime, M. Preparation of (3R,4R)-3-hydroxy-4-hydroxymethyl-
4-butanolide. Eur. Pat. Appl. Ep 581215 A2 19940202, 1994
(10) Francisco, M. C.; Nasser, A. L. M.; Lopes, L. M. X. Tetrahy-
droisoquinoline alkaloids and 2-deoxyribonolactones from Aris-
tolochia arcuata. Phytochemistry 2003, 62, 1265-1270, and
references therein.
(11) (a) Martin, T.; Martin, V. S. A short synthesis of trans-(+)-
laurediol. Tetrahedron Lett. 2000, 41, 2503-2505. (b) Garcia,
J M034216Y