A convenient one-step method for the preparation of alkynyl phenyl sulfides using diphenyl disulfide has been developed. The oxidation of the corresponding sulfides to the sulfoxides, and not sulfones, was achieved by using trans-(phenylsulfonyl)-3-phenyloxaziridine. A variety of other oxidizing reagents was also investigated.
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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 key 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.Key words: Sporormia affinis, cryptosporiopsin, chlorocyclopentenone, dichloroketene, [2+2] cycloaddition, ring expansion, selenium dioxide.
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
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