Document Detail

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.
MedLine Citation:
PMID:  9433759     Owner:  NLM     Status:  MEDLINE    
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.
K Yamada; H Iwadare; T Mukaiyama
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Chemical & pharmaceutical bulletin     Volume:  45     ISSN:  0009-2363     ISO Abbreviation:  Chem. Pharm. Bull.     Publication Date:  1997 Dec 
Date Detail:
Created Date:  1998-03-02     Completed Date:  1998-03-02     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0377775     Medline TA:  Chem Pharm Bull (Tokyo)     Country:  JAPAN    
Other Details:
Languages:  eng     Pagination:  1898-905     Citation Subset:  IM    
Department of Applied Chemistry, Faculty of Science, Science University of Tokyo, Japan.
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MeSH Terms
Bicyclo Compounds / chemical synthesis*,  chemistry
Bridged Compounds / chemical synthesis*,  chemistry
Diterpenes / chemical synthesis*,  chemistry
Ketones / chemistry
Lactones / chemical synthesis,  chemistry
Magnetic Resonance Spectroscopy
Reg. No./Substance:
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

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