Canadian Forest Service Publications

A new short synthetic approach to chlorocyclopentenones related to cryptosporiopsin via a ring expansion strategy: first synthesis of a fungitoxic metabolite from Sporormia affinis. 2000. Kabanyane, S.; Decken, A.; Yu, C.-M.; Strunz, G.M. Canadian Journal of Chemistry 78: 270-274.

Year: 2000

Issued by: Atlantic Forestry Centre

Catalog ID: 6070

Language: English

Availability: Order paper copy (free)

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Abstract

A metabolite of the coprophilous fungus, Sporormia affinis, 2-trans-allyl-5-chloro-1-hydroxy-4-oxo-2-cyclopentene-1-carboxylic acid methyl ester, 2, was synthesized in racemic form, by an eight-step sequence, in 11% overall yield. Departing from previous ring-contraction strategies for synthesis of chlorocyclopentenones in the cryptosporiopsin series, the dey step in the new synthesis was ring expansion of a substituted cyclobutanone, the product of [2+2] cycloaddition of dichloroketene with methyl 2-trimethylsilyloxyhex-2-enoate.