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8686359 
Journal Article 
Stereochemical Course of the Robinson Annelation Reaction. cis-9-Hydroxy-10-methyldecalin-2,5-dione 
Spencer, TA; Neel, HS; Ward, DC; Williamson, KL 
1966 
Yes 
Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 
31 
2 
434-436 
English 
cis-9-Hydroxy-10-methyldecalin-2,5-dione (III) has been prepared by careful pyrrolidine-catalyzed cyclization of 2-methyl-2-(3-oxobutyl)cyclohexane-l,3-dione (I). Piperidine-catalyzed cyclization of I afforded a mixture of III and bridged ketol IV. Conversion of the known β-epoxide VI to III defined the stereochemistry of the ketol, which is cis, as expected. 1966, American Chemical Society. All rights reserved.