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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 |

REPOSITORIES: biostudies-literature

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