The Journal of Organic Chemistry

A practical synthesis of rosefuran. Furans from acetylenes and allyl alcohols

BM Trost, JA Flygare

Index: Trost, Barry M.; Flygare, John A. Journal of Organic Chemistry, 1994 , vol. 59, # 5 p. 1078 - 1082

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Citation Number: 60

Abstract

A new atom-economical synthetic strategy for the synthesis of furans emerges from j3, y- unsaturated ketones which are readily available from, acetylenes and allyl alcohols by simple additions in the presence of a ruthenium catalyst. Dihydroxylation using catalytic osmium tetraoxide creates a diol that is remarkably prone to cyclize to furans in the presence of an acid catalyst. The novelty of this synthesis lies in the overall strategy whereby furans ...

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