Document Detail


Synthesis of (-)-deoxoprosophylline, (+)-2-epi-deoxoprosopinine, and (2R,3R)- and (2R,3S)-3-hydroxypipecolic acids from D-glycals.
MedLine Citation:
PMID:  20524655     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
New syntheses of (-)-deoxoprosophylline, (+)-2-epi-deoxoprosopinine, and (2R,3R)- and (2R,3S)-3-hydroxypipecolic acids are reported. Utilization of the chiral functionalities of Perlin aldehydes, derived from 3,4,6-tri-O-benzyl glycals, has been done along with chemoselective saturation of olefins and reductive aminations as key steps.
Authors:
Hari Prasad Kokatla; Rima Lahiri; Pavan K Kancharla; Venkata Ramana Doddi; Yashwant D Vankar
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  75     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2010 Jul 
Date Detail:
Created Date:  2010-06-25     Completed Date:  2010-11-22     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4608-11     Citation Subset:  IM    
Affiliation:
Department of Chemistry, Indian Institute of Technology Kanpur 208 016, India.
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MeSH Terms
Descriptor/Qualifier:
Alkaloids / chemical synthesis*,  chemistry*
Benzyl Compounds / chemistry*
Molecular Structure
Pipecolic Acids / chemical synthesis*,  chemistry*
Piperidines / chemical synthesis*,  chemistry*
Pyrans / chemical synthesis*,  chemistry*
Stereoisomerism
Chemical
Reg. No./Substance:
0/2-hydroxymethyl-6-dodecylpiperidin-3-ol; 0/3-hydroxypipecolic acid; 0/Alkaloids; 0/Benzyl Compounds; 0/Pipecolic Acids; 0/Piperidines; 0/Pyrans; 0/deoxoprosopinine

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