Epoxide-Opening Cascades in the Synthesis of Polycyclic Polyether Natural Products

• Published in: Angewandte Chemie (International ed.) Vol. 48; no. 29; pp. 5250 - 5281
• Main Authors: Vilotijevic, Ivan, Jamison, Timothy F
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley-VCH Verlag 06.07.2009; WILEY-VCH Verlag; WILEY‐VCH Verlag
• Subjects: Biological Products - chemical synthesis; Biological Products - chemistry; biomimetic synthesis; epoxides; Epoxy Compounds - chemical synthesis; Epoxy Compounds - chemistry; Ethers - chemical synthesis; Ethers - chemistry; Molecular Structure; natural products; polycycles; Polycyclic Aromatic Hydrocarbons - chemical synthesis; Polycyclic Aromatic Hydrocarbons - chemistry; polyethers
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.200900600

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.