4.8 Article

Total Synthesis of Bipolamine I

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 144, Issue 28, Pages 12638-12641

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c06015

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Funding

  1. NIH [R35GM139583]

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In this study, a stereoselective 15-step synthesis of Bipolamine I was reported, which can serve as a method to access other polypyrrole natural products and key analogues. This research is of great significance for the study of semi-synthetic indolizidine alkaloids.
Indolizidine alkaloids have been the target of chemical and biological studies for decades, most recently highlighted by the isolation of the curvulamine and bipolamine polypyrrole-containing subclass. Herein we report a stereoselective 15-step synthesis of bipolamine I, a distinct member of the broader family, and through this work develop an intermediate that will serve to access other polypyrrole natural products and key analogues going forward.

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