Synthetic transformations of higher terpenoids: XIV. Synthesis of pyrrololabdanoids from lambertianic acid

SV Chernov, EE Shul'ts, MM Shakirov…

Index: Chernov; Shul'ts; Shakirov; Tolstikov Russian Journal of Organic Chemistry, 2006 , vol. 42, # 6 p. 828 - 838

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Citation Number: 10

Abstract

Abstract Treatment of lambertianic acid methyl ester with lead tetraacetate gave terpenoid 2, 5-diacetoxydihydrofuran which reacted with primary amines to yield 3-terpenyl-substituted pyrrol-2 (5 H)-ones; the reaction with hydrazine led to the corresponding pyridazine derivative. The obtained furanoterpenoids underwent oxidative methoxylation by the action of N-chlorobenzenesulfonamide or N-bromosuccinimide in methanol. 2, 5- ...