A synthesis of herboxidiene

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-activato...

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Bibliographic Details
Published inJournal of the Chemical Society, Perkin Transactions 1 no. 8; pp. 955 - 968
Main Authors Blakemore, PR, Kocienski, PJ, Morley, A, Muir, K
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 1999
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALCOHOLS
DESS-MARTIN PERIODINANE
TETRAHYDROPYRANOID CORE
POLYKETIDE HERBICIDE HERBOXIDIENE
SIDE-CHAIN
ASYMMETRIC DIHYDROXYLATION
FRAGMENT
A7847
MODEL
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Summary: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 alpha,beta-unsaturated eater. Key steps in the synthesis of the C11-C19 polyketide fragment were (a) a directed aldol reaction using a camphor-10,2-sultam as auxiliary; (b) an Ireland-Claisen rearrangement and (c) a hydroxy-directed epoxidation.
ISSN:0300-922X
1364-5463
DOI:10.1039/a900185i