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An Oxidative Prins-Pinacol Tandem Process Mediated by a Hypervalent Iodine Reagent: Scope, Limitations and Applications.
MedLine Citation:
PMID:  21988536     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
An oxidative Prins-Pinacol tandem process mediated by a hypervalent iodine reagent has been developed. This oxidative version of the famous tandem process fits within the concept of "aromatic ring umpolung", and allows the stereoselective transformation of simple phenols into highly elaborated spirocyclic dienone cores containing several quaternary carbon centers. The scope and the limitations of this process, including the study of its stereoselectivity, are described in this article. As a direct application of this stereoselective process, we describe the formal synthesis of (-)-platensimycin, an important antibiotic agent.
Authors:
Marc-Andre Beaulieu; Kimiaka Chantal Guerard; Gaëtan Maertens; Cyrille Sabot; Sylvain Canesi
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-10-11
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  -     Publication Date:  2011 Oct 
Date Detail:
Created Date:  2011-10-12     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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