Total Synthesis of Jerangolid B via sp3-sp2 Stille Coupling

Abstract

First isolated from Sorangium cellulosum So ce 307, jerangolids are a class of natural products with high antifungal activity and minimal toxicity toward mammals. Comprised of a skipped diene substructure with a chiral center in between a δ-lactone and a pyran substituent, they present an intriguing synthetic challenge. We herein report the first synthesis of jerangolid B through a modular approach that incorporates sp3–sp2 Stille coupling as the key step to generate the skipped diene structure. By comparing our synthetic jerangolid B to the data published in the literature, we could show that the configuration at C14 is R.