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|Type:||Artigo de periódico|
|Title:||STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-INVICTOLIDE - AN EFFICIENT PREPARATION OF A TRISUBSTITUTED DELTA-LACTONE FROM ALDOL PRECURSORS|
|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|
|Appears in Collections:||Artigos e Materiais de Revistas Científicas - Unicamp|
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