Diterpenoids. XXXVIII. Conversion of l-abietic acid into steroidal skeletons: Formation of the D-ring. I.

• 田原 昭

• 嶋垣 正之

• 伊藤 正善

• 針谷 義弘

• 恩田 政行

抄録

The steroidal D-rings (31 and 37), along with 32 and 38, were synthesized by the use of a part or whole of the carbon units of the isopropyl group of l-abietic acid (1), via oxidation of 18 or 20 with Tl (ONO₂)₃, or addition reaction of 20 with 1, 1-dichloroethylene, and modifications of the functionality, followed by Friedel-Crafts cyclization. Cyclization to the 14-position (formation of 31 or 37) in 30 or 35 was always predominant over that to the 12-position (formation of 32 or 38). In attempts for functionalization of the isopropyl group with Pb (OAc)₄, 9, a hopeful intermediate to syntheseze quinoid diterpenes, was obtained via 3, 4, 5 and 6. RuO₂ reduction of 6 and successive Pb (OAc)₄ oxidation to 17 is also described.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 23 (12), 3189-3202, 1975

  公益社団法人 日本薬学会

キーワード

• Drug Discovery
• General Chemistry
• General Medicine

詳細情報

• CRID: 1390282679145536640
• NII論文ID: 110003621829
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.23.3189
• COI: 1:CAS:528:DyaE28XptVensw%3D%3D
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/23/12/23_12_3189/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1977059481
• 本文言語コード: en
• データソース種別:
  • JaLC
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可