A short, stereodivergent synthesis of the racemic erythro and threo diastereomers of 6-acetoxy-5-hexadecanolide, a mosquito oviposition attractant pheromone

Jefford, Charles; Jaggi, Danielle; Boukouvalas, John

doi:10.1016/S0040-4039(00)84897-2

Scientific article

English

A short, stereodivergent synthesis of the racemic erythro and threo diastereomers of 6-acetoxy-5-hexadecanolide, a mosquito oviposition attractant pheromone

ContributorsJefford, Charles; Jaggi, Danielle; Boukouvalas, John

Published inTetrahedron letters, vol. 27, no. 34, p. 4011-4014

Publication date1986

Abstract

A versatile 3-step synthesis of the title lactones has been accomplished by the stereocontrolled addition of n-decylmetallic reagents to acrolein dimer. Stereocontrol of the first step enables selective synthesis of either diastereomeric lactone.

Affiliation entities

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

Citation (ISO format)

JEFFORD, Charles, JAGGI, Danielle, BOUKOUVALAS, John. A short, stereodivergent synthesis of the racemic erythro and threo diastereomers of 6-acetoxy-5-hexadecanolide, a mosquito oviposition attractant pheromone. In: Tetrahedron letters, 1986, vol. 27, n° 34, p. 4011–4014. doi: 10.1016/S0040-4039(00)84897-2

Article (Published version)

Identifiers

PID : unige:167132
DOI : 10.1016/S0040-4039(00)84897-2

Additional URL for this publicationhttps://linkinghub.elsevier.com/retrieve/pii/S0040403900848972

Journal ISSN0040-4039

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A short, stereodivergent synthesis of the racemic erythro and threo diastereomers of 6-acetoxy-5-hexadecanolide, a mosquito oviposition attractant pheromone

A versatile 3-step synthesis of the title lactones has been accomplished by the stereocontrolled addition of n-decylmetallic reagents to acrolein dimer. Stereocontrol of the first step enables selective synthesis of either diastereomeric lactone.

Technical informations