Facile synthesis of fucoserratene and the (.+-.)-dictyopterenes B, D, and D'(= ectocarpene): constituents of marine brown algae

MP Schneider, M Goldbach

Index: Schneider; Goldbach Journal of the American Chemical Society, 1980 , vol. 102, # 19 p. 6114 - 6116

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Citation Number: 34

Abstract

Abstract: A low step approach to the title compounds 1-4 has been developed by employing three highly stereo-or regiochemically controlled reactions:(a) a Z-stereoselective Wittig reaction;(b) a 1, 3-dipolar cycloaddition;(c) a Cope rearrangement. A Z-stereoselective Wittig reaction of (E)-2, 4-pentadienal (10) with n-propylidenetriphenylphosphorane leads to fucoserratene (1) with 97% Z configuration at C (5). 1, 3-Dipolar cycloaddition of 3-diazo-1 ...

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