| Complementary diastereoselective reduction of cyclic gamma-keto acids: efficient access to trisubsituted gamma-lactones. | |
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MedLine Citation:
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PMID: 15624989 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Complementary reduction conditions have been identified that provide ready access to each respective diastereomer of bi- and tricyclic, trisustituted gamma-lactones starting from the corresponding cyclic gamma-keto acids. Subjection of cyclic gamma-keto acids to silane reagents in the presence of trifluoroacetic acid provides all syn-gamma-lactones, while reduction with trialkylborohydrides furnishes the syn,anti-gamma-lactones. The conditions are mild and provide the product lactones in good yields and modest to excellent selectivity. |
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Authors:
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Eric A Bercot; David E Kindrachuk; Tomislav Rovis |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Organic letters Volume: 7 ISSN: 1523-7060 ISO Abbreviation: Org. Lett. Publication Date: 2005 Jan |
Date Detail:
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Created Date: 2004-12-30 Completed Date: 2006-06-09 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: 107-10 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Keto Acids
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chemistry* Lactones / chemistry* Oxidation-Reduction Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Keto Acids; 0/Lactones |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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