| Synthesis of (-)-pericosine B, the antipode of the cytotoxic marine natural product. | |
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MedLine Citation:
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PMID: 19109676 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Yoshihide Usami; Kentaro Suzuki; Koji Mizuki; Hayato Ichikawa; Masao Arimoto |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2008-11-13 |
Journal Detail:
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Title: Organic & biomolecular chemistry Volume: 7 ISSN: 1477-0539 ISO Abbreviation: Org. Biomol. Chem. Publication Date: 2009 Jan |
Date Detail:
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Created Date: 2008-12-25 Completed Date: 2009-02-13 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 101154995 Medline TA: Org Biomol Chem Country: England |
Other Details:
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Languages: eng Pagination: 315-8 Citation Subset: IM |
Affiliation:
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Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. usami@gly.oups.ac.jp |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Biological Products
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chemical synthesis,
toxicity Cell Line, Tumor Humans Shikimic Acid / analogs & derivatives*, chemical synthesis, toxicity Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Biological Products; 0/pericosine B; 138-59-0/Shikimic Acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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