Synthetic studies toward the marine metabolite prorocentin-4: synthesis of the C1–C23 fragment

Abstract

A synthetic study of the construction of the C1–C23 fragment of prorocentin-4, a novel linear polyketide, is described. The synthetic highlights include the acid catalyzed epoxide opening, Gilman reaction, Pd(OH)₂ catalyzed transformation of a primary propargylic alcohol into an aldehyde, Oxa-Michael cyclization, and Horner–Wadsworth–Emmons (HWE) olefination reaction as key steps.