Tetrahedron

A novel and efficient route to chiral A-ring aromatic trichothecanes—The first enantiocontrolled total synthesis of (-)-debromofiliformin and (-)-filiformin

…, J Miyata, H Hakamata, M Nagamochi, K Fukumoto

Index: Nemoto, Hideo; Miyata, Junji; Hakamata, Hideki; Nagamochi, Masatoshi; Fukumoto, Keiichiro Tetrahedron, 1995 , vol. 51, # 19 p. 5511 - 5522

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Citation Number: 41

Abstract

The first examples of asymmetric dihydroxylation (AD) of the cyclopropylidene derivatives 12a∼ e followed by enantiospecific 1, 2-rearrangement of the resulted diols 13a∼ e to give the optically active cyclobutanones 15a∼ d and 11, and also the first enantiocontrolled total synthesis of (-)-debromofiliformin (7a) and (-)-filiformin (7b) starting from 11via the regiocontrolled cyclization of the phenolic allyl alcohol 25 to the A-ring aromatic ...