A synthesis of herboxidiene

PR Blakemore, PJ Kocieński

Index: Blakemore, Paul R.; Kocienski, Philip J.; Morley, Andrew; Muir, Kenneth Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 8 p. 955 - 968

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Citation Number: 73

Abstract

The natural herbicide herboxidiene was constructed from two key fragments using a modified Julia olefination based on the benzothiazolyl sulfone activator. Key steps in the synthesis of the C1–C10 oxane fragment were (a) a modified Julia olefination using a 1- phenyl-1H-tetrazolyl sulfone as activator and (b) an intramolecular addition of an alkoxide to an α, β-unsaturated ester. Key steps in the synthesis of the C11–C19 polyketide fragment ...