| Efficient intramolecular asymmetric reductions of alpha-, beta-, and gamma-keto acids with diisopinocampheylborane. | |
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MedLine Citation:
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PMID: 11429859 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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[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. |
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Authors:
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P V Ramachandran; H C Brown; S Pitre |
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Publication Detail:
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Type: Journal Article; Research Support, U.S. Gov't, Non-P.H.S. |
Journal Detail:
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Title: Organic letters Volume: 3 ISSN: 1523-7060 ISO Abbreviation: Org. Lett. Publication Date: 2001 Jan |
Date Detail:
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Created Date: 2001-06-29 Completed Date: 2001-07-19 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 100890393 Medline TA: Org Lett Country: United States |
Other Details:
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Languages: eng Pagination: 17-8 Citation Subset: IM |
Affiliation:
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Herbert C. Brown Center for Borane Research, Purdue University, West Lafayette, Indiana 47907-1393, USA. chandran@purdue.edu |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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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:
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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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