Document Detail


Characterization of an abeo-taxane: brevifoliol and derivatives.
MedLine Citation:
PMID:  15165147     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Brevifoliol is a natural diterpene isolated from Taxus baccata Nutt. A series of brevifoliol 1 derivatives, 2-8 and 10, were prepared for characterization and semisynthesis purposes and included the introduction of acetyl, Troc, and TES groups at C-5 and C-13. Derivatives 16-20 of 5-acetylbrevifoliol 2 were obtained via esterification with cinnamic acid, with both 2S-(-)- and 2R-(+)-3-phenyllactic acid, and with N-benzoyl-(2'R,3'S)-3'-phenylisoserine at C-13. Brevifoliol compounds 12, 13, and 15 with either 2S-(-)-phenyllactate moieties at C-5 and C-13 or an N-benzoyl-(2'R,3'S)-3'-phenylisoserinyl at C-13 were also prepared. An abeo-taxane structure for 1 was clearly defined from the (13)C NMR analysis of the 5-acetyl-13-oxo derivative 8 and from the conversion of 1 into 10, a conformationally restrained compound having a C-13, C-15 oxygen bridge. The biological activity of each of these derivatives is being studied.
Authors:
Steve Tremblay; Chantal Soucy; Neil Towers; Philip J Gunning; Livain Breau
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of natural products     Volume:  67     ISSN:  0163-3864     ISO Abbreviation:  J. Nat. Prod.     Publication Date:  2004 May 
Date Detail:
Created Date:  2004-05-28     Completed Date:  2004-06-24     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  7906882     Medline TA:  J Nat Prod     Country:  United States    
Other Details:
Languages:  eng     Pagination:  838-45     Citation Subset:  IM    
Affiliation:
Département de Chimie, Université du Québec à Montréal, C.P. 8888 Succ. Centre-Ville, Montréal (PQ), Canada, H3C 3P8.
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MeSH Terms
Descriptor/Qualifier:
Catalysis
Esterification
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plants, Medicinal / chemistry*
Stereoisomerism
Structure-Activity Relationship
Taxoids / chemical synthesis,  chemistry*
Taxus / chemistry*
Chemical
Reg. No./Substance:
0/Taxoids; 0/brevifoliol

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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