Macrolactonization via Ti(IV)-Mediated Epoxy-Acid Coupling: A Total Synthesis of (−)-Dactylolide [and Zampanolide]
- 17 July 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (32) , 9576-9577
- https://doi.org/10.1021/ja035579q
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.Keywords
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