| A novel, one-pot ring expansion of cyclobutanones. Syntheses of carbovir and aristeromycin. | |
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MedLine Citation:
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PMID: 10750497 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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A novel, one-pot ring-expansion procedure was developed using Me3S(O)I, NaH, and Sc(OTf)3. The scope and limitations were briefly examined, and a tentative mechanism was proposed. Application of the methodology to known cyclobutanone 1 provided the corresponding cyclopentanone, which was successfully advanced to (+)-carbovir and (+)-aristeromycin. |
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Authors:
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B Brown; L S Hegedus |
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Publication Detail:
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Type: Journal Article; Research Support, U.S. Gov't, P.H.S. |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 65 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2000 Mar |
Date Detail:
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Created Date: 2000-05-08 Completed Date: 2000-05-08 Revised Date: 2007-11-14 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 1865-72 Citation Subset: IM; X |
Affiliation:
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Department of Chemistry, Colorado State University, Fort Collins 80523, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Adenosine
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analogs & derivatives*,
chemical synthesis Anti-HIV Agents / chemical synthesis* Butanones / chemical synthesis* Dideoxynucleosides / chemical synthesis* Stereoisomerism |
| Grant Support | |
ID/Acronym/Agency:
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GM26178/GM/NIGMS NIH HHS; GM49631/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Anti-HIV Agents; 0/Butanones; 0/Dideoxynucleosides; 118353-05-2/carbovir; 19186-33-5/aristeromycin; 58-61-7/Adenosine |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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