A summary of studies providing a first generation and second generation total synthesis of vindoline based on the implementation of a powerful [4+2]/[3+2] cycloaddition cascade of 1,3,4-oxadiazoles will be presented along with its extension to the preparation of a series of key analogs. The development of a single-step biomimetic Fe(III)-promoted coupling of vindoline with catharanthine and subsequent in situ oxidation to provide vinblastine, its extension to the total synthesis of related natural products and key analogs will be summarized. Use of this technology in key studies addressing the structural features of vinblastine contributing to its tubulin binding and antitumor properties, and the synthesis, evaluation, and discovery of potent and improved analogs will be highlighted.

Vinblastine: Synthetic and mechanistic studies

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.