36 (±)および(+)-Nootkatonesの合成

• 鳥居 滋

  岡大・工

• 井口 勉

  岡大・工

• 浅沼 五朗

  岡大・工

• 小川 英則

  岡大・工

書誌事項

タイトル別名

• 36 Synthetic Studies of (+)- and (+)-Nootkatones

抄録

Synthetic strategies for the preparation of (±)- and (+)-nootkatones (1), the latter of which is known as an important odoriferous constituent of grapefruit, are described. A) (±)-1 was obtained by allylic oxidation of (±)-valencene (18), starting from 4β,10β-dimethyloctalone ethylene acetal 4 by stereocontrolled functionalizations involving the introduction of isopropenyl group at the C-6 position and the formation of double bond at the C-1(10) position leading to 18. B-1) Two different synthetic strategies discussed for the preparation of (+)-1 involve following ideas: one is elongation of carbon chain of keto ester 23 by the intramolecular alkylation of 28, reduction of the exo-methylene group of 36, and subsequent oxidative fission of the enolic olefin of 37 leading to acetonyl ketone 25, a key precursor of (+)-1; the other deals with the functionalization of tricyclo[7.1.1.0]undec-7-ene derivative 43 prepared from nopadiene and ethyl α-acetoxyacrylate by the Diels-Alder reaction by i) reductive methylation of epoxy ketone 46 to introduce the angular methyl group, ii) 1,4-addition of methyl group of dienone 50, and iii) isomerization of 4β-methyl group to 4α-isomer 55.

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 24 (0), 277-283, 1981

  天然有機化合物討論会実行委員会

詳細情報

• CRID: 1390282681050002176
• NII論文ID: 110006678240
• DOI: 10.24496/tennenyuki.24.0_277
• 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