24 2-Deoxycrustecdysoneの全合成

• 亀谷 哲治

  星薬大

• 津吹 政可

  星薬大

• 日暮 勝之

  星薬大

• 加藤 正

  星薬大

• 本多 利雄

  星薬大

書誌事項

タイトル別名

• 24 TOTAL SYNTHESIS OF 2-DEOXYCRUSTECDYSONE

抄録

The stereocontrolled synthesis of steroid side chain has been developed. The major interest has been forcused on the synthesis of the side chain of ecdysone as well as crustecdysone from 20-oxosteroid via furan derivatives. Reduction of the olefin (21) over palladium-carbon afforded the (20S)-20-furylsteroid (22), stereoselectively, whose hydrogenation over rhodium-alumina, followed by ruthenium tetroxide oxidation and treatment with methylmagnesium bromide, gave the triols (28) and (29) having an ecdysone-type side chain, respectively. The stereoselective reduction of the lactone (33) as a key reaction to give the δ-lactone (35) and the γ-lactone (36), under various conditions has also been investigated. Grignard reaction of both lactones with methylmagnesium bromide led to the synthesis of the tetraol (37) possessing a crustecdysone side chain. The total synthesis of 2-deoxycrustecdysone (3) has also been achieved by application of the above method.

収録刊行物

• 天然有機化合物討論会講演要旨集

  天然有機化合物討論会講演要旨集 27 (0), 176-183, 1985

  天然有機化合物討論会実行委員会

詳細情報

• CRID: 1390282681050529152
• NII論文ID: 110006678456
• DOI: 10.24496/tennenyuki.27.0_176
• ISSN: 24331856
• 本文言語コード: ja
• データソース種別:
  • JaLC
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可