Journal
NATURAL PRODUCT REPORTS
Volume 31, Issue 4, Pages 504-513Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3np70076c
Keywords
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Funding
- Robert A. Welch Foundation [F-0038]
- NIH-NIGMS [RO1-GM093905]
- CPRIT
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Despite the longstanding importance of polyketide natural products in human medicine, nearly all commercial polyketide-based drugs are prepared through fermentation or semi-synthesis. The paucity of manufacturing routes involving de novo chemical synthesis reflects the inability of current methods to concisely address the preparation of these complex structures. Direct alcohol C-H bond functionalization via C-C bond forming transfer hydrogenation provides a powerful, new means of constructing type I polyketides that bypasses stoichiometric use of chiral auxiliaries, premetallated C-nucleophiles, and discrete alcohol-to-aldehyde redox reactions. Using this emergent technology, total syntheses of 6-deoxyerythronolide B, bryostatin 7, trienomycins A and F, cyanolide A, roxaticin, and formal syntheses of rifamycin S and scytophycin C, were accomplished. These syntheses represent the most concise routes reported to any member of the respective natural product families.
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