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- Title
Concise, Enantioselective, and Versatile Synthesis of (−)-Englerin A Based on a Platinum-Catalyzed [4C+3C] Cycloaddition of Allenedienes.
- Authors
Nelson, Ronald; Gulías, Moisés; Mascareñas, José L.; López, Fernando
- Abstract
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.
- Subjects
ENANTIOSELECTIVE catalysis; PLATINUM catalysts; RING formation (Chemistry); ALLENE; DIOLEFINS
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 46, p14571
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201607348