| Stereoselective synthesis of unnatural spiroisoxazolinoproline-based amino acids and derivatives. | |
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MedLine Citation:
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PMID: 12153267 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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A route to spiroisoxazolinoproline-based amino acid derivatives is reported in which exo-methyleneprolinate 4 (tert-butyl ester) reacts as a dipolarophile with nitrile oxides to generate spiroisoxazolinoprolinates 7/10/11 in good yields (70-75%) and with ca. 1:4 cis:trans diastereoselectivity. tert-Butyl spiroisoxazolinoprolinates were separable by column chromatography and amenable to scale-up leading to single diastereoisomers of N-Boc and N-Fmoc protected spiroisoxazolinoproline amino acids. |
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Authors:
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Wei-Chieh Cheng; Yannan Liu; Melissa Wong; Marilyn M Olmstead; Kit S Lam; Mark J Kurth |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S. |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 67 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2002 Aug |
Date Detail:
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Created Date: 2002-08-02 Completed Date: 2002-09-20 Revised Date: 2006-11-15 |
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: 5673-7 Citation Subset: IM |
Affiliation:
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Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616-5295, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Amino Acids
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chemical synthesis*,
chemistry Models, Molecular Molecular Conformation Oxazoles* Proline / analogs & derivatives*, chemistry Stereoisomerism Structure-Activity Relationship |
| Chemical | |
Reg. No./Substance:
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0/Amino Acids; 0/Oxazoles; 147-85-3/Proline |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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