Document Detail

Stereochemistry of sagittamide A: prediction and confirmation.
MedLine Citation:
PMID:  16898837     Owner:  NLM     Status:  MEDLINE    
[structure: see text] The C5-C10 relative stereochemistry of sagittamide A was predicted, with the use of the 3JH,H profiles assembled from the spin-coupling constants reported in the literature. The predicted relative stereochemistry was then confirmed by a total synthesis of two relevant remote diastereomers. The absolute configuration of sagittamide A was established through a detailed 1H NMR analysis of the two remote diastereomers, followed by doping experiments of them with the authentic natural product.
Hirofumi Seike; Indranath Ghosh; Yoshito Kishi
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Organic letters     Volume:  8     ISSN:  1523-7060     ISO Abbreviation:  Org. Lett.     Publication Date:  2006 Aug 
Date Detail:
Created Date:  2006-08-10     Completed Date:  2007-06-13     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  3865-8     Citation Subset:  IM    
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
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MeSH Terms
Biological Products / chemistry
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Ornithine / analogs & derivatives*,  chemistry
Valine / analogs & derivatives*,  chemistry
Reg. No./Substance:
0/Biological Products; 0/sagittamide A; 7004-03-7/Valine; 7006-33-9/Ornithine
Erratum In:
Org Lett. 2006 Oct 26;8(22):5177

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