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

M Yoshimatsu, M Naito, H Shimizu…

Index: Yoshimatsu, Mitsuhiro; Naito, Motoyo; Shimizu, Hiroshi; Muraoka, Osamu; Tanabe, Genzoh; Kataoka, Tadashi Journal of Organic Chemistry, 1996 , vol. 61, # 23 p. 8200 - 8206

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Citation Number: 14

Abstract

2-Ethoxy-4-(phenylchalcogeno) but-3-ynyl ketones 1-10 were reduced with LiBH4 in Et2O 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.