Issue 9, 1978

Synthesis of tertiary acyloins using acyl anions formed from 1,3-dithians. Total synthesis of (±)-(2E)-1,7-dihydroxy-3,7,11-trimethyl-dodeca-2,10-dien-6-one

Abstract

An advantageous approach for the synthesis of tertiary acyloins has been studied. The results were used in designing a successful synthesis of (±)-(2E)-1,7-dihydroxy-3,7,11-trimethyldodeca-2,10-dien-6-one (18). This acyloin was synthesized by alkylation of 2-acyl-1,3-dithians (7a and b) with (2E)-5-iodo-3-methylpent-2-en-1-ol tetrahydropyranyl ether (10). The synthesis of the key intermediate (10) is reported. This type of modified farnesol can be used for investigating the biosynthetic intermediates of natural substances.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1978, 1036-1041

Synthesis of tertiary acyloins using acyl anions formed from 1,3-dithians. Total synthesis of (±)-(2E)-1,7-dihydroxy-3,7,11-trimethyl-dodeca-2,10-dien-6-one

L. Colombo, C. Gennari, C. Scolastico and M. G. Beretta, J. Chem. Soc., Perkin Trans. 1, 1978, 1036 DOI: 10.1039/P19780001036

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