Document Detail


SmI(2)-induced reductive cyclizations for the synthesis of cyclic ethers and applications in natural product synthesis.
MedLine Citation:
PMID:  20502797     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
This tutorial review covers SmI(2)-induced reductive cyclizations of beta-alkoxyacrylate, beta-alkoxyvinyl sulfone, and beta-alkoxyvinyl sulfoxide, as methods for efficient construction of cyclic ethers. These cyclizations were developed as tools to aid in the total synthesis of marine polycyclic ethers, whose complex, synthetically challenging structures and potent bioactivities have attracted the attention of numerous synthetic organic chemists. Applications of the methods to total syntheses of various natural products containing cyclic ether are also described.
Authors:
Tadashi Nakata
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Publication Detail:
Type:  Journal Article; Review     Date:  2010-03-23
Journal Detail:
Title:  Chemical Society reviews     Volume:  39     ISSN:  1460-4744     ISO Abbreviation:  Chem Soc Rev     Publication Date:  2010 Jun 
Date Detail:
Created Date:  2010-05-26     Completed Date:  2010-08-25     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0335405     Medline TA:  Chem Soc Rev     Country:  England    
Other Details:
Languages:  eng     Pagination:  1955-72     Citation Subset:  IM    
Affiliation:
Department of Chemistry, Faculty of Science, Tokyo University of Science, 1-3, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan. nakata@rs.kagu.tus.ac.jp
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MeSH Terms
Descriptor/Qualifier:
Biological Products / chemical synthesis*,  chemistry
Cyclization
Ethers, Cyclic / chemical synthesis*,  chemistry
Iodides / chemistry*
Samarium / chemistry*
Stereoisomerism
Chemical
Reg. No./Substance:
0/Biological Products; 0/Ethers, Cyclic; 0/Iodides; 0/samarium diiodide; 7440-19-9/Samarium

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