Stereospecific Syntheses of 5-Alkyl-3-ethoxy-2-((phenylchalcogeno)methylene)tetrahydrofurans

Mitsuhiro Yoshimatsu; Motoyo Naito; Hiroshi Shimizu; Osamu Muraoka; Genzoh Tanabe; Tadashi Kataoka

doi:10.1021/jo961071c

Stereospecific Syntheses of 5-Alkyl-3-ethoxy-2-((phenylchalcogeno)methylene)tetrahydrofurans

J Org Chem. 1996 Nov 15;61(23):8200-8206. doi: 10.1021/jo961071c.

Authors

Mitsuhiro Yoshimatsu¹, Motoyo Naito, Hiroshi Shimizu, Osamu Muraoka, Genzoh Tanabe, Tadashi Kataoka

Affiliation

¹ Gifu University, Faculty of Education, Yanagido, Gifu 501-11, Japan, Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502, Japan, and Kinki University, Faculty of Pharmaceutical Sciences, 3-4-1, Kowakae, Higashi-osaka, Osaka 577, Japan.

PMID: 11667807
DOI: 10.1021/jo961071c

Abstract

2-Ethoxy-4-(phenylchalcogeno)but-3-ynyl ketones 1-10 were reduced with LiBH(4) in Et(2)O diastereoselectively to give 5-(phenylchalcogeno)pent-4-yn-1-ols 11-20. Treatment of the phenylchalcogen-substituted alkynyl alcohols 11-20 with t-BuOK in t-BuOH provided useful (Z)-2-((phenylchalcogeno)methylene)tetrahydrofurans 21-31 stereoselectively.