Document Detail

Complementary stereocontrolled approaches to 2-pyrrolidinones bearing a vicinal amino diol subunit with three continuous chiral centers: a formal asymmetric synthesis of (-)-detoxinine.
MedLine Citation:
PMID:  17949109     Owner:  NLM     Status:  MEDLINE    
We report herein two stereocomplementary approaches to erythro/trans and threo/cis vicinal amino diol subunits containing 2-pyrrolidinones (9 and 10) starting from the known enamides 7, easily available from malimides. The first approach consists of an epoxidation-reductive dehydroxylation procedure, and the second one is based on hydroboration-oxidation reactions. Using the second method, a formal asymmetric synthesis of (-)-detoxinine was achieved.
Xiang Zhou; Wen-Jun Liu; Jian-Liang Ye; Pei-Qiang Huang
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2007-10-20
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  72     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2007 Nov 
Date Detail:
Created Date:  2007-11-02     Completed Date:  2008-01-07     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  8904-9     Citation Subset:  IM    
Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, PR China.
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MeSH Terms
Amino Alcohols / chemical synthesis*,  chemistry*
Crystallography, X-Ray
Models, Molecular
Molecular Conformation
Pyrrolidines / chemical synthesis*,  chemistry
Pyrrolidinones / chemical synthesis*,  chemistry
Reg. No./Substance:
0/Amino Alcohols; 0/Pyrrolidines; 0/Pyrrolidinones; 0/detoxinine; 616-45-5/2-pyrrolidone

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