Total synthesis of cavicularin and riccardin C: Addressing the synthesis of an arene that adopts a boat configuration

DC Harrowven, T Woodcock…

Index: Harrowven, David C.; Woodcock, Timothy; Howes, Peter D. Angewandte Chemie - International Edition, 2005 , vol. 44, # 25 p. 3899 - 3901

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Citation Number: 64

Abstract

From a structural perspective cavicularin (1), from the liverwort Cavicularia densa,[1] is one of the most unusual natural products to have been isolated in the last decade. It comprises a macrocyclic core that contains dibenzyl and dihydrophenanthrene units conjoined by a biaryl bond and an ether linkage. This core imparts such strain on the system that one of the arenes, ring A, adopts a boatlike configuration and is twisted out of the plane by some 158 ...