| Stereoselective total synthesis of cis- and trans-3-hydroxypipecolic acid. | |
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MedLine Citation:
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PMID: 16292869 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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[reaction: see text] 3-Hydroxypipecolic acid, a nonproteinogenic cyclic alpha-amino acid, is a common structural moiety found in a large number of natural and synthetic compounds of medicinal significance. Utilizing D-serine as a chiral template, the present research describes efficient and straightforward routes to cis- and trans-3-hydroxypipecolic acids in enantiopure form. The key steps in the syntheses involve chelation-controlled addition of a homoallyl Grignard reagent to a protected serinal derivative toward stereoselective formation of the corresponding syn-amino alcohol adduct 3. On the other hand, zinc borohydride-mediated chelation-controlled reduction of a serine-derived alpha-aminoketone precursor leads to the formation of the corresponding anti-amino alcohol adduct 4 with high stereoselectivity. Following an efficient sequence of reactions, the above amino alcohol derivatives were subsequently transformed to the corresponding cis- and trans- title compounds, respectively. |
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Authors:
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Ningning Liang; Apurba Datta |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 70 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2005 Nov |
Date Detail:
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Created Date: 2005-11-18 Completed Date: 2006-07-10 Revised Date: - |
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: 10182-5 Citation Subset: IM |
Affiliation:
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Department of Medicinal Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Molecular Structure Picolinic Acids / chemical synthesis*, chemistry Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Picolinic Acids; 874-24-8/3-hydroxypicolinic acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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