Document Detail

Efficient intramolecular asymmetric reductions of alpha-, beta-, and gamma-keto acids with diisopinocampheylborane.
MedLine Citation:
PMID:  11429859     Owner:  NLM     Status:  MEDLINE    
[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.
P V Ramachandran; H C Brown; S Pitre
Related Documents :
22118819 - Preactivated thiomers as mucoadhesive polymers for drug delivery.
420789 - Catalytic action of l-methionine gamma-lyase on selenomethionine and selenols.
2576059 - The effect of monoamine depletors on metrazol induced convulsions and brain gamma-amino...
891869 - Neurochemical correlates of alloxan diabetes: gamma amino butyric acid of amphibian brain.
20488039 - Carnosine, homocarnosine and anserine in vertebrate retinas.
1968959 - Comparison of transmitter amino acid levels in rat globus pallidus and neostriatum duri...
7979549 - Effect of dietary omega-3 and omega-6 fatty acid sources on puva-induced cutaneous toxi...
2193009 - Synthesis and structure determination of fr109615, a new antifungal antibiotic.
2551389 - Identification of na+/k+-atpase inhibitors in bovine plasma as fatty acids and hydrocar...
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    
Herbert C. Brown Center for Borane Research, Purdue University, West Lafayette, Indiana 47907-1393, USA.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Boron Compounds / chemistry*
Keto Acids / chemistry*
Lactones / chemical synthesis*,  chemistry*
Molecular Conformation
Molecular Structure
Pheromones* / chemistry,  secretion
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

Previous Document:  The copper-mediated cross-coupling of phenylboronic acids and N-hydroxyphthalimide at room temperatu...
Next Document:  Neisseria gonorrhoeae 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase does not catalyze the for...