Opening of Aryl-Substituted Epoxides To Form Quaternary Stereogenic Centers:  Synthesis of (−)-Mesembrine

Cycloalkanones are easily converted into aryl-substituted cyclic alkenes by the addition of an aryl Grignard reagent followed by dehydration. These alkenes are good substrates for asymmetric epoxidation. We have found that the addition of allylic and benzylic Grignard reagents can occur preferential...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 70; no. 19; pp. 7711 - 7714
Main Authors Taber, Douglass F, He, Yigang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.09.2005
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Indole Alkaloids - chemical synthesis
Physical Sciences
Science & Technology
Stereoisomerism
CYCLOADDITION
ROUTE
ASYMMETRIC-SYNTHESIS
REAGENTS
CARBON CENTER
EFFICIENT SYNTHESIS
ALLYLIC ALKYLATION
SCELETIUM
ENANTIOSELECTIVE CONSTRUCTION
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Summary:Cycloalkanones are easily converted into aryl-substituted cyclic alkenes by the addition of an aryl Grignard reagent followed by dehydration. These alkenes are good substrates for asymmetric epoxidation. We have found that the addition of allylic and benzylic Grignard reagents can occur preferentially at the benzylic position of the derived epoxides to give the quaternary stereogenic center. This approach led to a short synthesis of the nanomolar serotonin re-uptake inhibitor (−)-mesembrine.
Bibliography:istex:F5124B44E4782E513551C182403694EFFF56D03D
ark:/67375/TPS-17C3W0SW-0
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This work is dedicated to the memory of Conrad J. Kowalski, a master of the science and art of organic synthesis.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0511039