Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Diterpenoids. XXXI. Reaction of Methyl Dehydroabietate Derivatives with Aluminum Chloride under Effect of Electron-withdrawing Group. Synthesis of Methyl Deisopropyldehydroabietate Series
AKIRA TAHATAHIROYUKI AKITA
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JOURNAL FREE ACCESS

1975 Volume 23 Issue 9 Pages 1984-1988

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Abstract
Reaction of 12-acetyl ester (5) with aluminum chloride gave predominant trans-isomer (6) in company with the cis (7). trans-Isomer had not been observed as major product in the reactions of methyl dehydroabietate having electron-donating group at aromatic ring as described previously. In the other cases of reactions of methyl dehydroabietate derivatives having electron-withdrawing group, 7-oxo ester (20) did not react even under the drastic condition. But 7-oxo ester having a hydroxyl or a methoxyl group at 12-or 14-position was deisopropylated to give only the respective trans deisopropyl isomer.
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© The Pharmaceutical Society of Japan
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