Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 7, Pages 2674-2678Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201913730
Keywords
catalysis; oxygenation; Pd; total synthesis; triquinanes
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Funding
- University of Chicago
- National Institutes of Health [R01-GM132570]
- Bristol-Myers Squibb
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Pd-catalyzed sequences involving oxidative addition, cyclization, and termination through intermolecular nucleophile capture have tremendous utility. Indeed, they can generate a plethora of different polycyclic structures possessing a diverse range of functionality. However, one area of deficiency for Pd-0/Pd-II variants is the ability to conclude them with oxygen-based species. Inspired by the recent discovery of one such reaction in the course of a total synthesis program, we delineate herein that it has significant strength, both in terms of substrate scope as well as the terminating oxygen nucleophile. As a result, the reaction proved critical in achieving total syntheses of two oxygenated natural products, one of which was prone to over-oxidation. Finally, a mechanistic proposal that accounts for its success is provided.
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