Document Detail

Total synthesis of (-)-kainic acid via intramolecular Michael addition: a second-generation route.
MedLine Citation:
PMID:  18402455     Owner:  NLM     Status:  MEDLINE    
A total synthesis of (-)-kainic acid starting from the commercially available 2-azetidinone is described. The key delta-lactone intermediate was concisely prepared from the commercially available azetidinone through the Reformatsky-type reaction and an introduction of a glycine moiety. The construction of the functionalized pyrrolidine ring was executed by a one-pot sequential elimination-Michael addition protocol of a beta-amino-delta-lactone intermediate with high diastereoselectivity.
Hiroshi Sakaguchi; Hidetoshi Tokuyama; Tohru Fukuyama
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2008-04-11
Journal Detail:
Title:  Organic letters     Volume:  10     ISSN:  1523-7060     ISO Abbreviation:  Org. Lett.     Publication Date:  2008 May 
Date Detail:
Created Date:  2008-04-24     Completed Date:  2008-08-07     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1711-4     Citation Subset:  IM    
Graduate School of Pharaceutical Sciences, University of Tokyo, Tokyo, Japan.
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MeSH Terms
Algae / chemistry
Azetidines / chemistry
Kainic Acid / chemical synthesis*,  chemistry
Lactones / chemistry
Molecular Structure
Pyrrolidines / chemistry
Reg. No./Substance:
0/2-azetidinone; 0/Azetidines; 0/Lactones; 0/Pyrrolidines; 123-75-1/pyrrolidine; 487-79-6/Kainic Acid

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