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Convenient synthesis of decalin systems of bioactive terpenoids

✍ Scribed by Vinayak K Gore; Shailesh R Desai; T Mayelvaganan; R Padmakumar; Shreeshailkumar B Hadimani; Sujata V Bhat

Book ID
104203923
Publisher
Elsevier Science
Year
1993
Tongue
French
Weight
948 KB
Volume
49
Category
Article
ISSN
0040-4020

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✦ Synopsis

Recently Wenkert and coworkers 11 reported a broad study of Duels-Alder reaction of cyclohexenones with various 1,3-dienes under Lewis acid catalysis. However, Welzel and coworkers described 12 unsuccessful attempt of synthesis of A,B-ring system of forskolin through thermal Diels-Alder reaction of 4,4-dimethyl-cyclohexenone with silyloxy dienes. These authors subsequently synthesised A,B-rings of forskolin through Pumerer type reaction of sulfoxide obtained from 4,4-dimethyl-cyclohexenone. We report herein our studies on Diels-Alder reaction between the dlenone 71Β° and various 1,2-disubstituted -1,3-dlenes 8a-k, subsequent deformylatlon, eplmerisation, angular methylation, oxidation and reduction of the adducts (Figure 2).

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