Synthetic Studies on the Lycopodium Alkaloids. III. Synthesis of a Key Intermediate, Ethyl Octahydro-4aβ-hydroxy-7β-methyl-10-oxo-1H-5, 8α-propanoquinoline-1-carbamate, for the Lycopodium Alkaloids

• 堀井 善一

• 金 相元

• 今西 武

• 百瀬 雄章

抄録

A tricyclic key intermediate (II) for the lycopodine and the lycodine type of alkaloids was synthesized from 9-oxobicyclo (3, 3, 1) nonene system (IV) by a series of reactions shown in Chart 2. Dehydration of II with strong acid resulted in the rearrangement of carbon skeleton into an enamino-ketone (III). The stereochemistry of stereoselective C₉-alkylation in IV with sulfonium ylid was also discussed.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 18 (11), 2235-2241, 1970

  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: 1390282679145931776
• NII論文ID: 110003654583
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.18.2235
• COI: 1:CAS:528:DyaE3MXkt1Ghsw%3D%3D
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/18/11/18_11_2235/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1971087757
• 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