Catalytic Asymmetric Total Synthesis of (+)-Yohimbine

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 intr...

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Bibliographic Details
Published inOrganic letters Vol. 10; no. 5; pp. 745 - 748
Main Authors Mergott, Dustin J, Zuend, Stephan J, Jacobsen, Eric N
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.03.2008
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Cyclization
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
Yohimbine - chemical synthesis
Yohimbine - chemistry
ALCOHOLS
ESTER
YOHIMBINE
ORIGINS
CYCLIZATIONS
SERIES
DIELS-ALDER REACTIONS
STEREOSELECTIVITY
TRANSITION-STATES
INDOLE ALKALOIDS
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Summary: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.
Bibliography:Medline
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ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol702781q