Chemical communications

Concise synthesis of the (±)-N b-desmethyl-meso-chimonanthine

C Menozzi, PI Dalko, J Cossy

Index: Menozzi, Candice; Dalko, Peter I.; Cossy, Janine Chemical Communications, 2006 , # 44 p. 4638 - 4640

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Citation Number: 15

Abstract

We wish to report herein a highly convergent approach to N b -desmethyl-meso-chimonanthine (3), the structurally simplest member of this class of alkaloid, which can provide access to more complex desymmetrised pyrrolidinoindoline alkaloids. The key step of the sequence is a diastereoselective tandem [4 + 2]-cycloaddition–cyclisation, inspired by the elegant synthesis of (±)-perophoramidine achieved by Fuchs and Funk. 14 We envisaged that this reaction could be applied in the ...

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