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.
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.M.A. Gennari, C. Scolastico, M.G. Beretta. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - 9(1978), pp. 1036-1041. [10.1039/P19780001036]
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
C.M.A. Gennari;C. Scolastico;
1978
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.
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