Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 46, Pages 14357-14361Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201607348
Keywords
allenes; asymmetric catalysis; cycloaddition; guaiane natural products; total synthesis
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Funding
- Spanish MINECO [SAF2013-41943-R]
- ERDF
- ERC [340055]
- Xunta de Galicia [GRC2013-041, 2015-CP082]
- Orfeo-cinqa [CTQ2014-51912-REDC]
- CONICYT-Becas Chile
- European Research Council (ERC) [340055] Funding Source: European Research Council (ERC)
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A practical synthesis of (-)-englerin A was accomplished in 17 steps and 11% global yield from commercially available achiral precursors. The key step consists of a platinum-catalyzed [4C+3C] allenediene cycloaddition that directly delivers the trans-fused guaiane skeleton with complete diastereoselectivity. The high enantioselectivity (99% ee) stems from an asymmetric ruthenium-catalyzed transfer hydrogenation of a readily assembled diene-ynone. The synthesis also features a highly stereoselective oxygenation, and a late-stage cuprate alkylation that enables the preparation of previously inaccessible structural analogues.
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