Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 353, Issue 17, Pages 3213-3226Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201100579
Keywords
asymmetric catalysis; dynamic kinetic resolution; hydrogenation; ruthenium; total synthesis
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Funding
- Ministere de l'Enseignement Superieur et de la Recherche
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A concise, enantioselective total synthesis of symbioramide, starting from simple achiral compounds and racemic alpha-amino-beta-keto ester derivatives is reported. This highly flexible strategy allowed the efficient preparation of seven structural isomers of the natural product as well. The synthesis relies on a convergent route that involves the efficient stereoselective reduction of a alpha-keto-beta-yne ester, and the dynamic kinetic resolution of an alpha-amino-beta-keto ester through ruthenium-mediated asymmetric hydrogenation.
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