Total Synthesis of (−)-Zampanolide and Questionable Existence of (−)-Dactylolide as the Elusive Biosynthetic Precursor of (−)-Zampanolide in an Okinawan Sponge
Organic Letters2009Vol. 11(15), pp. 3262–3265
Citations Over TimeTop 10% of 2009 papers
Abstract
A new and concise total synthesis of (-)-zampanolide, (-)-1, and (-)-dactylolide, (-)-2, is described. Synthetic highlights include (i) a mild Horner-Wadsworth-Emmons reaction providing the seco acid, (ii) an unusual stepwise cross-coupling reaction of a 1,1-dibromodiene with inversion of olefin geometry, and (iii) specific O-Michael reaction conditions using catalytic LHMDS with TMEDA for the synthesis of functionalized 2,6-cis-tetrahydropyran. A marine sponge extract was analyzed for the presence of (-)-2 as the biosynthetic precursor of (-)-zampanolide.
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