| Construction of AB-ring system of taxane framework by A-ring annulation strategy: synthesis of 1-hydroxy-8,11,11-trimethylbicyclo-[5.3.1]undec-7-en-9-one by way of intramolecular aldol cyclization to form the C1-C10 bond. | |
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MedLine Citation:
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PMID: 9433759 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Construction of the AB-ring system of the taxane framework via an A-ring annulation strategy was demonstrated by base-mediated intramolecular aldol reaction of (Z)-2,2-dimethyl-3-(1-methyl-2-oxopropylidene)cyclooctanone, affording the title compound, 1-hydroxy-8,11,11-trimethylbicyclo[5.3.1]undec-7-en-9-one. A cyclization precursor, the tetra-substituted (Z)-alkene, was prepared from the corresponding cyclooctanone derivative, 3-[(alpha,alpha- dimethylbenzyl)dimethylsiloxy]-2,2-dimethylcyclooctanone via a bicyclic alpha,beta-unsaturated lactone intermediate. |
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Authors:
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K Yamada; H Iwadare; T Mukaiyama |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Chemical & pharmaceutical bulletin Volume: 45 ISSN: 0009-2363 ISO Abbreviation: Chem. Pharm. Bull. Publication Date: 1997 Dec |
Date Detail:
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Created Date: 1998-03-02 Completed Date: 1998-03-02 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 0377775 Medline TA: Chem Pharm Bull (Tokyo) Country: JAPAN |
Other Details:
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Languages: eng Pagination: 1898-905 Citation Subset: IM |
Affiliation:
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Department of Applied Chemistry, Faculty of Science, Science University of Tokyo, Japan. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Bicyclo Compounds
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chemical synthesis*,
chemistry Bridged Compounds / chemical synthesis*, chemistry Cyclization Cyclooctanes* Diterpenes / chemical synthesis*, chemistry Ketones / chemistry Lactones / chemical synthesis, chemistry Magnetic Resonance Spectroscopy Stereoisomerism Taxoids* |
| Chemical | |
Reg. No./Substance:
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0/1-hydroxy-8,11,11-trimethylbicyclo(5.3.1)undec-7-en-9-one; 0/Bicyclo Compounds; 0/Bridged Compounds; 0/Cyclooctanes; 0/Diterpenes; 0/Ketones; 0/Lactones; 0/Taxoids; 1605-68-1/taxane; 502-49-8/cyclooctanone |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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