Stereoselective Transformation of Enantiopure Cyclohexenol into cis-Hydrindan. An Enantioselective Formal Total Synthetic Route to (+)-Pumiliotoxin C

…, T Asoh, M Matsuura, K Fukumoto

Index: Toyota, Masahiro; Asoh, Takanobu; Matsuura, Masaki; Fukumoto, Keiichiro Journal of Organic Chemistry, 1996 , vol. 61, # 24 p. 8687 - 8691

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Citation Number: 32

Abstract

Pumiliotoxin C (1) 1 was originally isolated from the skin extracts of Dendrobates pumilio (a striking colored Panamanian poison arrow frog2). X-ray analysis3 of the crystalline hydrochloride of 1 established the structure, and the absolute configuration (2S, 4aS, 5R, 8aR) of this toxin was confirmed in 1977 by its total synthesis. 4 Because of the scarcity of natural material (eg, 15 mg of 1 from 250 frogs) 5 coupled with the intriguing ...