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.

SUBMITTER: Schug J 

PROVIDER: S-EPMC12281574 | biostudies-literature | 2025 Jul

REPOSITORIES: biostudies-literature