Document Detail

Synthesis of (-)-pericosine B, the antipode of the cytotoxic marine natural product.
MedLine Citation:
PMID:  19109676     Owner:  NLM     Status:  MEDLINE    
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.
Yoshihide Usami; Kentaro Suzuki; Koji Mizuki; Hayato Ichikawa; Masao Arimoto
Related Documents :
19924876 - Asymmetric total synthesis of (+)-crassalactone d.
12583776 - Total synthesis of (-)-21-isopentenylpaxilline.
19722666 - Total synthesis and structural revision of (+/-)-tricholomalides a and b.
20936666 - Total synthesis of dictyodendrins a-e.
17654046 - Nitrosylmyoglobin as antioxidant--kinetics and proposed mechanism for reduction of hydr...
10993206 - Mulberry leaf extract inhibits the oxidative modification of rabbit and human low densi...
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    
Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Biological Products / chemical synthesis,  toxicity
Cell Line, Tumor
Shikimic Acid / analogs & derivatives*,  chemical synthesis,  toxicity
Reg. No./Substance:
0/Biological Products; 0/pericosine B; 138-59-0/Shikimic Acid

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

Previous Document:  Biocatalytical production of (5S)-hydroxy-2-hexanone.
Next Document:  Formylnitroenamines: useful building blocks for nitrated pyridones and aminopyridines with functiona...