Regiocontrolled formation of 4, 5-dihydro-3 (2H)-furanones from 2-butyne-1, 4-diol derivatives. Synthesis of bullatenone and geiparvarin.

H Saimoto, T Hiyama, H Nozaki

Index: Saimoto, Hiroyuki; Hiyama, Tamejiro; Nozaki, Hitosi Bulletin of the Chemical Society of Japan, 1983 , vol. 56, # 10 p. 3078 - 3087

Full Text: HTML

Citation Number: 32

Abstract

Two new methods for selective hydration of 1, 1, 4-trisubstituted 2-butyne-1, 4-diols (1) to give 4, 5-dihydro-3 (2H)-furanone derivatives are reported. The first involves selective monoacetylation of the less hindered hydroxyl group of 1 followed by Ag (I)-catalyzed rearrangement and cyclization to give 3-acetoxy-2, 2, 5-trisubstituted 2, 5-dihydrofurans (2). Final hydrolysis yielded 2, 2, 5-trisubstituted 4, 5-dihydro-3 (2H)-furanones. Oxidation of ...