Document Detail


Synthesis of (-)-pericosine B, the antipode of the cytotoxic marine natural product.
MedLine Citation:
PMID:  19109676     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The stereoselective synthesis of (-)-pericosine B, which is the antipode of the cytotoxic metabolite of the fungus Periconia byssoides OUPS-N133 separated from the sea hare, was accomplished in 9 steps in 12% total yield from (-)-quinic acid, together with the synthesis of its epimer. Every crucial step of this total synthesis, including ring opening of a beta-epoxide and NaBH4 reduction of an unstable beta,gamma-unsaturated enone, proceeded with excellent stereoselectivity.
Authors:
Yoshihide Usami; Kentaro Suzuki; Koji Mizuki; Hayato Ichikawa; Masao Arimoto
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2008-11-13
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  7     ISSN:  1477-0539     ISO Abbreviation:  Org. Biomol. Chem.     Publication Date:  2009 Jan 
Date Detail:
Created Date:  2008-12-25     Completed Date:  2009-02-13     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101154995     Medline TA:  Org Biomol Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  315-8     Citation Subset:  IM    
Affiliation:
Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. usami@gly.oups.ac.jp
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MeSH Terms
Descriptor/Qualifier:
Biological Products / chemical synthesis,  toxicity
Cell Line, Tumor
Humans
Shikimic Acid / analogs & derivatives*,  chemical synthesis,  toxicity
Stereoisomerism
Chemical
Reg. No./Substance:
0/Biological Products; 0/pericosine B; 138-59-0/Shikimic Acid

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