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Review
Epoxide-Opening Cascades in the Synthesis of Polycyclic Polyether Natural Products
Article first published online: 1 JUL 2009
DOI: 10.1002/anie.200900600
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Vilotijevic, I. and Jamison, T. (2009), Epoxide-Opening Cascades in the Synthesis of Polycyclic Polyether Natural Products. Angewandte Chemie International Edition, 48: 5250–5281. doi: 10.1002/anie.200900600
Publication History
- Issue published online: 1 JUL 2009
- Article first published online: 1 JUL 2009
- Manuscript Received: 2 FEB 2009
- Abstract
- Article
- References
- Cited By
Keywords:
- biomimetic synthesis;
- epoxides;
- natural products;
- polycycles;
- polyethers
Graphical Abstract
The structural features of polycyclic polyether natural products can, in some cases, be traced to their biosynthetic origin. However in case that are less well understood, only biosynthetic pathways that feature dramatic, yet speculative, epoxide-opening cascades are proposed. We summarize how such epoxide-opening cascade reactions have been used in the synthesis of polycyclic polyethers (see scheme) and related natural products.
Abstract
The structural features of polycyclic polyether natural products can, in some cases, be traced to their biosynthetic origin. However in case that are less well understood, only biosynthetic pathways that feature dramatic, yet speculative, epoxide-opening cascades are proposed. We summarize how such epoxide-opening cascade reactions have been used in the synthesis of polycyclic polyethers (see scheme) and related natural products.
The group of polycyclic polyether natural products is of special interest owing to the fascinating structure and biological effects displayed by its members. The latter includes potentially therapeutic antibiotic, antifungal, and anticancer properties, and extreme lethality. The polycyclic structural features of this class of compounds can, in some cases, be traced to their biosynthetic origin, but in others that are less well understood, only to proposed biosynthetic pathways that feature dramatic, yet speculative, epoxide-opening cascades. In this review we summarize how such epoxide-opening cascade reactions have been used in the synthesis of polycyclic polyethers and related natural products.