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- Title
Development and Elucidation of a Pd‐Based Cyclization–Oxygenation Sequence for Natural Product Synthesis.
- Authors
Yi, Heng; Hu, Pengfei; Snyder, Scott A.
- Abstract
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 Pd0/PdII 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.
- Subjects
NATURAL products; OXIDATIVE addition; HECK reaction
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 7, p2696
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201913730