A new synthesis of (±)-myodesmone

Archives of Pharmacal Research - Tập 16 - Trang 205-208 - 1993
Oee Sook Park1, Hyun Joo Hwang1, Woo Young Lee2
1Department of Chemistry, Chungbuk National University, Chungbuk, Korea
2Department of Chemistry, Seoul National University, Seoul, Korea

Tóm tắt

(±)-Myodesmone was synthesized, starting from 2-cyclopentenone. The key reaction involved α-dimethoxymethylation of 2-cyclopentenone and organocopper conjugate addition reaction.

Tài liệu tham khảo

Blackburne, I. D., Park, R. J. and Sutherland, M. D., Terpenoid Chemistry XVIII. Myodesmone and Isomyodesmone, Toxic furanoid ketones fromMyoporum deserti andM. acuminatum.Aust. J. Chem., 24, 995–1007 (1971). Branca, J. and Smith, A. B., A Stereospecific total synthesis of (±)-Pentenomycin I, (±)-Pentenomycin II, and Dehydropentenomycin I. A versatile latent α-ketovinyl anion eqivalent.J. Am. Chem. Soc., 100, 7767–7768, (1978). Corey, E. J. and Enders, D., Synthetic routes to polyfunctional molecules via metallated N,N-dimethyl-hydrazones.Tetrahedrone Lett., 11–14 (1976). Dieter, R. K. and Dieter, J. W., Total Synthesis of (±)-Myodesmone employing a regiospecifically substituted α-oxoketone dithioacetal.J. Chem. Soc., Chem. Commun., 1378–1380 (1983). Fadel, A., Yefsah, R. and Sala, N. J., Anhydrous iron(III) chloride dispersed on silica gel; III. A convenient and mild reagent for deacetalization in dry medium.Synthesis., 37–40 (1987). Itoh, A., Ozawa, S., Oshima, K. and No, H., Aldol reaction of aluminium enolate resulting from 1,4-addition of Me2AlSPh to α,β-unsaturated carbonyl compound. A 1-acylethenyl anion equivalent.Tetrahedron Lett., 21, 361–364 (1980). Kim, S., Kim, Y. G. and Park, J. H., A simple procedure for α-alkoxyalkylation of α,g-enones via pyridiniosilylation.Tetrahedron Lett., 52, 2043–2044 (1991). Perrin, D. D., Armarego, L. F. and Perrin, O. R., Purification of laboratory chemicals 2nd ed., Pergamon Press, New York, 1980. Shono, T., Matsumura, Y., Kashimura, S. and Hatanaka, K., One step joining reaction of thiolate anions, activated olefins, and carbonyl compounds.J. Am. Chem. Soc., 101, 4752–4753 (1979). Stork, G. and Benaim, J., Monoalkylation of α,β-unsaturated ketones via metalloenamines.J. Am. Chem. Soc., 93, 5938–5939 (1971). Stork, G. and Maldonado, L., Anions of protected cyanohydrins as acyl carbanion equivalents and their use in a new synthesis of ketones.J. Am. Chem. Soc., 93, 5286–5287 (1971). Stork, G. and Maldonado, L., Conjugate addition of acyl carbanion equivalents via the protected cyanohydrin method.J. Am. Chem. Soc., 96, 5272–5274 (1974). Suzuki, M., Kawagishi, T. and Noyori, R., A new procedure for α-alkoxyalkylation of α,β-unsaturated ketones.Tetrahedron Lett., 22, 1809–1812 (1981).