Document Detail


Efficient intramolecular asymmetric reductions of alpha-, beta-, and gamma-keto acids with diisopinocampheylborane.
MedLine Citation:
PMID:  11429859     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
[figure: see text] alpha-, beta-, and gamma-Keto acids are reduced with diisopinocampheylborane at room temperature to the corresponding hydroxy acids with predictable stereochemistry in very high ee. The gamma-hydroxy acids produced were conveniently cyclized to the corresponding lactones. This provides a simple synthesis of 4-hexanolide, a component of the pheromone secreted by the female dermestid beetle Trogoderma glabrum.
Authors:
P V Ramachandran; H C Brown; S Pitre
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, Non-P.H.S.    
Journal Detail:
Title:  Organic letters     Volume:  3     ISSN:  1523-7060     ISO Abbreviation:  Org. Lett.     Publication Date:  2001 Jan 
Date Detail:
Created Date:  2001-06-29     Completed Date:  2001-07-19     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  17-8     Citation Subset:  IM    
Affiliation:
Herbert C. Brown Center for Borane Research, Purdue University, West Lafayette, Indiana 47907-1393, USA. chandran@purdue.edu
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MeSH Terms
Descriptor/Qualifier:
Animals
Beetles
Boron Compounds / chemistry*
Catalysis
Female
Keto Acids / chemistry*
Lactones / chemical synthesis*,  chemistry*
Molecular Conformation
Molecular Structure
Pheromones* / chemistry,  secretion
Chemical
Reg. No./Substance:
0/4-hexanolide; 0/Boron Compounds; 0/Keto Acids; 0/Lactones; 0/Pheromones

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


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