Double Bond Migration on the 22(17→28)abeo-Lupane Skeleton

• 渕野 裕之

  Faculty of Pharmaceutical Sciences, Science University of Tokyo

• 野澤 修

  Faculty of Pharmaceutical Sciences, Science University of Tokyo

• 田中 信壽

  Faculty of Pharmaceutical Sciences, Science University of Tokyo

抄録

Double bond migration on the 22(17→28)abeo-lupane skeleton was investigated using 28-p-toluenesulfonyloxy-lupane (4) and its 20(29)-ene derivative (7) as starting materials. In the case of 4,the double bond, formed between C-17 and C-28 after elimination of the p-toluenesulfonyloxy group followed by E-ring expansion, migrated to C-13 and C-18 under acidic conditions. In the case of 7,the double bond, formed after the elimination and the E-ring expansion, migrated in response to migration of the other double bond, 20(29)-ene, under acidic conditions. First, 20(29)-ene migrated to 19-ene (9), and then 17(28)-ene migrated to 13(18)-ene to form a conjugated 13 (18), 19-diene (10). Further migration proceeded to give an equilibrium mixture of 17α-H-11,13(18)-diene (11), 12,17-diene (12) and 17β-H-11,13(18)-diene (13) in a ratio of 3 : 3 : 5.

収録刊行物

• Chemical & pharmaceutical bulletin

  Chemical & pharmaceutical bulletin 42 (9), 1745-1749, 1994-09-15

  公益社団法人日本薬学会

キーワード

• double bond migration
• 22(17→28)abeo-lupane
• ring expansion
• 28-p-toluenesulfonyloxylupane
• 28-p-toluenesulfonyloxylup-20(29)-ene
• betulin

詳細情報

• CRID: 1573105977185646976
• NII論文ID: 110003631228
• NII書誌ID: AA00602100
• ISSN: 00092363
• 本文言語コード: en
• データソース種別:
  • CiNii Articles