Document Detail


Brønsted acid mediated cyclization of enaminones. Rapid and efficient access to the tetracyclic framework of the Strychnos alkaloids.
MedLine Citation:
PMID:  22257244     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The development of an efficient diastereoselective method that permits rapid construction of the tetracyclic core 17 of the Strychnos-Aspidosperma alkaloids is described. Enaminone 16, synthesized in high yield, has been cyclized under the influence of a Brønsted acid to provide the core tetracyclic framework 17 of the Strychnos alkaloids in optically active form or alternatively to the β-ketoester tetrahydro-β-carboline (THBC) unit 18, by varying the equivalents of acid and the molar concentration. Attempts to utilize 18 to form the C₇-C₁₆ bond of the akuammiline related alkaloids represented by strictamine (22), using metal-carbenoid chemistry, are also described.
Authors:
Rahul V Edwankar; Chitra R Edwankar; Ojas A Namjoshi; Jeffrey R Deschamps; James M Cook
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't     Date:  2012-01-18
Journal Detail:
Title:  Journal of natural products     Volume:  75     ISSN:  1520-6025     ISO Abbreviation:  J. Nat. Prod.     Publication Date:  2012 Feb 
Date Detail:
Created Date:  2012-02-24     Completed Date:  2012-04-23     Revised Date:  2014-09-19    
Medline Journal Info:
Nlm Unique ID:  7906882     Medline TA:  J Nat Prod     Country:  United States    
Other Details:
Languages:  eng     Pagination:  181-8     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Alkaloids / chemical synthesis,  chemistry
Cyclization
Indole Alkaloids / chemical synthesis*,  chemistry*
Molecular Structure
Stereoisomerism
Strychnos / chemistry*
Grant Support
ID/Acronym/Agency:
R01 MH046851/MH/NIMH NIH HHS; R01 MH046851-19/MH/NIMH NIH HHS; Y1-DA1101/DA/NIDA NIH HHS
Chemical
Reg. No./Substance:
0/Alkaloids; 0/Indole Alkaloids; 6475-05-4/strictamine
Comments/Corrections

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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