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.

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.
Settore CHIM/06 - Chimica Organica
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/176141
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 13
  • ???jsp.display-item.citation.isi??? ND
social impact