Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/75226
Type: Artigo de periódico
Title: STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-INVICTOLIDE - AN EFFICIENT PREPARATION OF A TRISUBSTITUTED DELTA-LACTONE FROM ALDOL PRECURSORS
Author: PILLI, RA
MURTA, MM
Abstract: The stereoselective total synthesis of (+/-)-invictolide (1), a component of the queen recognition pheromone of Solenopsis invicta, is described. The TiCl4-mediated addition of silyl ketene thioacetal 8 to (+/-)-3-(benzyloxy)-2-methylpropionaldehyde afforded exclusively thioester 10, in 65% yield, which was straightforwardly converted to diol 5 (ca. 31% yield). Diol 5 was also prepared after LiAlH4 reduction of the major aldol formed in the condensation between the lithium enolate of 2,6-di-tert-butyl-4-methylphenyl propanoate and (+/-)-2-methylvaleraldehyde (ca.50% overall yield). Intramolecular alkylation (t-BuOK-THF) of 6 or 7 gave a 40:60 mixture of (+/-)-1 and its C(3) epimer. Catalytic hydrogenation of unsaturated lactone 17 afforded (+/-)-1 in 80% yield.
Editor: Amer Chemical Soc
Rights: fechado
Identifier DOI: 10.1021/jo00054a014
Date Issue: 1993
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

Files in This Item:
File Description SizeFormat 
WOSA1993KH73800014.pdf631.36 kBAdobe PDFView/Open


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.