Document Detail


Stereoselective total synthesis of cis- and trans-3-hydroxypipecolic acid.
MedLine Citation:
PMID:  16292869     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
[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.
Authors:
Ningning Liang; Apurba Datta
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  70     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2005 Nov 
Date Detail:
Created Date:  2005-11-18     Completed Date:  2006-07-10     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  10182-5     Citation Subset:  IM    
Affiliation:
Department of Medicinal Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA.
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MeSH Terms
Descriptor/Qualifier:
Molecular Structure
Picolinic Acids / chemical synthesis*,  chemistry
Stereoisomerism
Chemical
Reg. No./Substance:
0/Picolinic Acids; 874-24-8/3-hydroxypicolinic acid

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