| Oxetanes from the ring contraction of alpha-triflates of gamma-lactones: oxetane nucleosides and oxetane amino acids. | |
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MedLine Citation:
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PMID: 21469449 Owner: NLM Status: In-Process |
Abstract/OtherAbstract:
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Alpha-Triflates of gamma-lactones with potassium carbonate in methanol give efficient contraction of the ring to oxetane-1-carboxylates in which the oxygen substituent at C(3) of the oxetane is predominantly trans to the carboxylate at C(2), regardless of the stereochemistry of the starting triflate. The limitations of the procedure are discussed and compared with analogous reactions for the preparation of THF carboxylates. The potential of the contraction in the preparation of oxetane nucleosides (such as oxetanocin) and oxetane sugar amino acids (analogues of oxetin) as peptidomimetics with predisposition to form secondary structural motifs is illustrated. |
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Authors:
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Sarah F Jenkinson; George W J Fleet |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Chimia Volume: 65 ISSN: 0009-4293 ISO Abbreviation: Chimia (Aarau) Publication Date: 2011 |
Date Detail:
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Created Date: 2011-04-07 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 0373152 Medline TA: Chimia (Aarau) Country: Switzerland |
Other Details:
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Languages: eng Pagination: 71-5 Citation Subset: IM |
Affiliation:
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Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, UK. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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