Solid-phase based total synthesis of Jasplakinolide by ring-closing metathesis

摘要

The study of classical ring-closing metathesis and relay ring-closing metathesis in a total synthesis of Jasplakinolide and its desbromo analog is described.rnNatural products are important tools for studies in chemical biology and medicinal chemistry, and, therefore, the development of new methodology for their synthesis is a major goal of organic chemistry.rnThe cyclodepsipeptide Jasplakinolide (Jaspamide, 1), isolated from marine sponges of the genus Jaspis, exhibits a remarkable bioactivity profile including antifungal, anthelminthic, insecticidal and anti-cancer activity (Scheme 1). Consequently, several total syntheses of 1 have been published all of which feature macrolactone formation as the cyclization method.