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Total synthesis of gonytolides C and G, lachnone C, and formal synthesis of blennolide C and diversonol.

Authors :
Sudhakar G
Bayya S
Kadam VD
Nanubolu JB
Source :
Organic & biomolecular chemistry [Org Biomol Chem] 2014 Aug 14; Vol. 12 (30), pp. 5601-10. Date of Electronic Publication: 2014 Jun 23.
Publication Year :
2014

Abstract

The first stereoselective total synthesis of gonytolide C, which is a monomeric unit of an innate immune promoter gonytolide A, has been accomplished from the aldol reaction between acetophenone derived from orcinol and butyrolactone containing α-keto ester followed by the excellent diastereoselective intramolecular cyclization. The first total synthesis of gonytolide G has been achieved by the oxidation of benzylic methyl in gonytolide C. Additionally, total synthesis of lachnone C and a formal synthesis of blennolide C and diversonol have been achieved by this synthetic method.

Details

Language :
English
ISSN :
1477-0539
Volume :
12
Issue :
30
Database :
MEDLINE
Journal :
Organic & biomolecular chemistry
Publication Type :
Academic Journal
Accession number :
24953777
Full Text :
https://doi.org/10.1039/c4ob00950a