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Type: Artigo de periódico
Title: Stereoselective Total Synthesis Of (±)-invictolide. An Efficient Preparation Of A Trisubstituted δ-lactone From Aldol Precursors
Author: Pilli R.A.
Murta M.M.
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. © 1993 American Chemical Society.
Rights: fechado
Identifier DOI: 
Date Issue: 1993
Appears in Collections:Unicamp - Artigos e Outros Documentos

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