Synthesis of Desepoxy-Tedanolide C.

ABSTRACT: The synthesis of desepoxy-tedanolide C was accomplished and provided experimental evidence on the configuration of tedanolide C. The reported chemical shifts and coupling constants point to a configuration different from the published structure and analogous to the structures of the other members of this family of natural products. The key step is a Kiyooka aldol protocol for the stereoselective synthesis of the tertiary alcohol flanked by three additional oxygenated carbon atoms. Furthermore, two additional aldol reactions and a Julia-Kocienski olefination were used to assemble the carbon framework.

SUBMITTER: Lucke D 

PROVIDER: S-EPMC8251979 | biostudies-literature | 2021 Apr

REPOSITORIES: biostudies-literature