Regioselective total synthesis of furoventalene, a marine natural benzofuran, via the. beta.-vinylbutenolide annulation

…, T Maruyama, C Kabuto, A Yoshikoshi

Index: Kido, Fusao; Noda, Yoshihiro; Maruyama, Takao; Kabuto, Chizuko; Yoshikoshi, Akira Journal of Organic Chemistry, 1981 , vol. 46, # 21 p. 4264 - 4266

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Citation Number: 14

Abstract

The framework of furoventalene (1) was regioselectively constructed from methyl 2-fomy1-6- methyl-~ heptenoate (12) and 2, 5-dihydro-3-methyl-4-vinyl-2-furanone (10) by consecutive 1, 6 conjugate addition and aldol-type cyclization to lead to a diastereomeric mixture of bicyclic butenolidea 13a and 13b. Both of the annulation products were transformed into 1 by a sequence of reactions: reduction, hydrolysis, dehydrative decarboxylation, and ...