Macrolactonization via Ti(IV)-mediated epoxy-acid coupling: A total synthesis of (-)-dactylolide [and zampanolide]

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Abstract

A total synthesis of dactylolide (1) is described. The key feature involves the Ti(IV)-mediated coupling of structurally complex "Sharpless epoxides" and carboxylic acids in either an intramolecular (macrolactonization) or an intermolecular mode. Other notable aspects include a proton-catalyzed, cis-selective construction of the 4-methylenetetrahydropyran ring; a selective oxidation of an allylic alcohol in the presence of a 1,2-diol by an oxoammonium ion; an efficient ring-closing metathesis reaction of an in situ (bis-TMS) protected α,ω-diene-vic-diol; and an aluminum-mediated aza-aldol reaction of a primary amide to 1 to construct the acyclic carbinolamide in zampanolide.

Original languageEnglish (US)
Pages (from-to)9576-9577
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number32
DOIs
StatePublished - Aug 13 2003

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