A direct synthesis of (±)-eldanolide <i>via</i> the highly regioselective prenylation of 2-trimethylsiloxyfuran

Jefford, Charles; Sledeski, Wojciech Adam; Boukouvalas, John

doi:10.1016/S0040-4039(00)95882-9

Scientific article

English

A direct synthesis of (±)-eldanolide via the highly regioselective prenylation of 2-trimethylsiloxyfuran

ContributorsJefford, Charles; Sledeski, Wojciech Adam; Boukouvalas, John

Published inTetrahedron letters, vol. 28, no. 9, p. 949-950

Publication date1987

Abstract

The reaction of 2-trimethylsiloxyfuran, 3,3-dimethylallyl bromide and silver trifluoroacetate produced (3,3-dimethylallyl)-4-but-2-en-4-olide with high double regiodifferentiation. The latter compound on treatment with lithium dimethylcuprate gave (±)-eldanolide in high yield.

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

JEFFORD, Charles, SLEDESKI, Wojciech Adam, BOUKOUVALAS, John. A direct synthesis of (±)-eldanolide via the highly regioselective prenylation of 2-trimethylsiloxyfuran. In: Tetrahedron letters, 1987, vol. 28, n° 9, p. 949–950. doi: 10.1016/S0040-4039(00)95882-9

Article (Published version)

Identifiers

PID : unige:166822
DOI : 10.1016/S0040-4039(00)95882-9

Additional URL for this publicationhttps://linkinghub.elsevier.com/retrieve/pii/S0040403900958829

Journal ISSN0040-4039

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A direct synthesis of (±)-eldanolide via the highly regioselective prenylation of 2-trimethylsiloxyfuran

The reaction of 2-trimethylsiloxyfuran, 3,3-dimethylallyl bromide and silver trifluoroacetate produced (3,3-dimethylallyl)-4-but-2-en-4-olide with high double regiodifferentiation. The latter compound on treatment with lithium dimethylcuprate gave (±)-eldanolide in high yield.

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