Tetrahedron Letters

First enantioselective total synthesis of (−)-dysibetaine CPa and absolute configurations of natural product

M Sakai, Y Ishikawa, S Takamizawa, M Oikawa

Index: Sakai, Michihiro; Ishikawa, Yuichi; Takamizawa, Satoshi; Oikawa, Masato Tetrahedron Letters, 2013 , vol. 54, # 44 p. 5911 - 5912

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Citation Number: 6

Abstract

Abstract Here we report total synthesis of enantiomerically pure dysibetaine CPa, isolated from Micronesian marine sponge and expected to serve as a neuroactive agent. Starting from meso-cyclopropane triester, the synthesis was achieved in 12.8% overall yield over 10 steps including organocatalytic enantioselective solvolysis of meso-succinic anhydride as a key step. This work established the absolute configurations of the natural product as (3R, ...