4.8 Article

Catalytic asymmetric total synthesis of (+)-yohimbine

Journal

ORGANIC LETTERS
Volume 10, Issue 5, Pages 745-748

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol702781q

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Funding

  1. NIGMS NIH HHS [GM-59316] Funding Source: Medline

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The total synthesis of (+)-yohimbine was achieved in 11 steps and 14% overall yield. The absolute configuration was established through a highly enantioselective thiourea-catalyzed acyl-Pictet-Spengler reaction, and the remaining 4 stereocenters were set simultaneously in a substrate-controlled intramolecular Diels-Alder reaction.

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