Chemical Studies on the Oriental Plant Drugs. XXVII. The Acid Catalyzed Reactions and the Absolute Configuration at C_<(20)> of Dammarane Type Triterpenes

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概要

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• On acid treatments, betulafolianetriol (VII) having the same configuration at C_<(20)> as dammarenediol II (VI) gave an equilibrated mixture of VII and its C_<(20)> epimer (VIII). The derivatives of betulafolienetriol (IV) and VII having a hydroxyl or methoxyl group at C_<(12)> also showed the configurational equilibration at C_<(20)> hydroxyl under the same condition, whereas those without hydroxyl or methoxyl at C_<(12)> showed no or negligible epimerization at C_<(20)>. The acid catalyzed pyran ring formation from the side chain of betulafolienetriol (IV) gave 3,20-epi-panaxadiol (XII) and 3-epi-panaxadiol (XI) by the retention and the inversion of its C_<(20)>-configuration, respectively. It reveals that C_<(20)>-configuration of panaxadiol (I) and protopanaxadiol (III) (epimeric at C_<(3)> and C_<(20)> of IV) are same as that of dammarenediol I (V). Since the chirality at C_<(20)> of panaxadiol (I) has already been established as R, dammarenediol I type triterpenes have (R)-configuration at C_<(20)>, and dammarenediol II type compounds S. This conclusion has also been supported by the IR-absorptions of C_<(20)> keto and C_<(20)> hydroxyl of 12-keto-3-acetates (XVII and XVIII) of betulafolianetriol (VII) and dihydroprotopanaxadiol (X). The mechanism of epimerization at C_<(20)> on the acid treatments of dammaran-20-olcompounds having O-function at C_<(12)> was discussed.

• 社団法人日本薬学会の論文
• 1972-06-25

著者

• 柴田 承二

  Meiji College of Pharmacy

• 田中 治

  Faculty Of Pharmaceutical Sciences University Of Tokyo:(present Address) Pharmaceutical Institute Sc

• 柴田 承二

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 大沢 富彦

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 田中 信寿

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 永井 正博

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 河合 賢一

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 田中 信寿

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 河合 賢一

  Faculty Of Pharmaceutical Sciences Hoshi University

• 柴田 承二

  明治薬科大学

• 永井 正博

  星薬科大学生薬学教室

• 永井 正博

  Faculty Of Pharmaceutical Sciences University Of Tokyo:(present Addresses)hoshi College Of Pharmacy

• 柴田 承二

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 大沢 富彦

  Faculty Of Pharmaceutical Sciences University Of Tokyo:(present Address) Institute For Chemical And

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