Studies of the synthesis of 8a-hydroxy-4a-methyloctahydronaphthalen-1(2H)-ones and their 2α-deutero derivatives

Two syntheses of the bicyclic α-ketols, 8a-hydroxy-4a-methyl-trans- and -cis-octahydronaphthalen-1(2H)-ones ( 1 and 2 ), have been effected. One involves epoxidation of 4a-methyl-1,2,3,4,4a,5,6,7-octahydronaphthalene ( 4 ), followed by hydrolysis and oxidation; direct "hydroxy ketonization"...

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Bibliographic Details
Published in:Canadian journal of chemistry 1988-01, Vol.66 (1), p.27-34
Main Authors: Stiver, Shirley, Clark, Peter D, Yates, Peter
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Summary:Two syntheses of the bicyclic α-ketols, 8a-hydroxy-4a-methyl-trans- and -cis-octahydronaphthalen-1(2H)-ones ( 1 and 2 ), have been effected. One involves epoxidation of 4a-methyl-1,2,3,4,4a,5,6,7-octahydronaphthalene ( 4 ), followed by hydrolysis and oxidation; direct "hydroxy ketonization" of 4 was found not to be practicable. The second involves treatment of 3,4,5,6,7,8-hexahydronaphthalen-1(2H)-one ( 14 ) with lithium dimethylcuprate, trimethylsilylation of the resulting enolate, oxidation of the enol ether, and hydrolysis. Syntheses of the 2α-deutero derivatives of 1 and 2 are also described.
ISSN:0008-4042
1480-3291
DOI:10.1139/v88-004