Journal
TETRAHEDRON LETTERS
Volume 59, Issue 39, Pages 3583-3585Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2018.08.046
Keywords
(+)-Bernumidine; Bernumidine enantiomer; MOR ligands; Chemoenzymatic DKR; Enantioselective hydrogenation
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Funding
- Sao Paulo Research Foundation (FAPESP) [2017/21990-0]
- National Council for Scientific and Technological Development (CNPq)
- Coordination of Improvement of Higher Level Personnel (CAPES)
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Total syntheses of (+)-bernumidine and its unnatural enantiomer were accomplished through chemoenzymatic dynamic kinetic resolution and ruthenium(II)-catalyzed enantioselective hydrogenation, which provided (R)-salsolidine propyl carbamate and N-acetyl (S)-salsolidine in high yields and enantiomeric excesses, respectively. Both enantiomers of salsolidine were accessed and converted into (+)- and (-)-bernumidine via simple and efficient transformations. (C) 2018 Elsevier Ltd. All rights reserved.
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