Regioselective alkylation of 2-trimethylsiloxyfuran; direct access to 4-substituted but-2-en-4-olides

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

doi:10.1039/C39880000364

Scientific article

English

Regioselective alkylation of 2-trimethylsiloxyfuran; direct access to 4-substituted but-2-en-4-olides

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

Published inJournal of the Chemical Society. Chemical communications, no. 5, p. 364-365

Publication date1988

Abstract

Primary iodides alkylate 2-trimethylsiloxyfuran in the presence of a molar excess of silver trifluoroacetate to give the 4-alkylbut-2-en-4-olides in 55–81% yield; as an illustration of the method, the cytotoxic marine sponge constituent, 4-(methoxycarbonylmethyl)but-2-en-4-olide was prepared in 79% yield in one step.

Affiliation entities

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

Citation (ISO format)

JEFFORD, Charles, SLEDESKI, Wojciech Adam, BOUKOUVALAS, John. Regioselective alkylation of 2-trimethylsiloxyfuran; direct access to 4-substituted but-2-en-4-olides. In: Journal of the Chemical Society. Chemical communications, 1988, n° 5, p. 364–365. doi: 10.1039/C39880000364

Article (Published version)

Identifiers

PID : unige:166468
DOI : 10.1039/C39880000364

Additional URL for this publicationhttp://xlink.rsc.org/?DOI=c39880000364

Journal ISSN0022-4936

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Regioselective alkylation of 2-trimethylsiloxyfuran; direct access to 4-substituted but-2-en-4-olides

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