Syntheses of Cecropia Juvenile Hormones by Selective Side-chain Methylation of (<i>E</i>,<i>E</i>)-Farnesol

• Yasuda Arata

  Department of Industrial Chemistry, Kyoto University

• Tanaka Shin

  Department of Industrial Chemistry, Kyoto University

• Yamamoto Hisashi

  Department of Industrial Chemistry, Kyoto University

• Nozaki Hitosi

  Department of Industrial Chemistry, Kyoto University

書誌事項

タイトル別名

• Syntheses of cecropia juvenile hormones by selective side-chain methylation of (E,E)-farnesol.

抄録

The stereoselective route to the title insect hormones (JH-1 & JH-2) depends crucially on the epoxidation of allylic alcohols with t-butyl hydroperoxide in the presence of oxobis(2,4-pentanedionato-O,O′)vanadium(IV). The oxidation of 2-methyl-1-hepten-3-ol exclusively produces the (2R^*,3S^*) isomerofthe diastereomeric epoxy alcohols. This is converted into (Z)-6-methyl-5-undecene by the sequence involving oxirane reaction with lithium dibutylcuprate(I) and the removal of both hydroxyl groups of the resulting 1,2-diol. Extension of the series of reactions to the mono- and bisoxirane derived from (E,E)-farnesol gives JH-2 and JH-1, respectively.

収録刊行物

• Bulletin of the Chemical Society of Japan

  Bulletin of the Chemical Society of Japan 52 (6), 1701-1704, 1979

  公益社団法人 日本化学会

キーワード

• General Chemistry

詳細情報

• CRID: 1390282679118541184
• NII論文ID: 130001968844
• DOI: 10.1246/bcsj.52.1701
• ISSN: 13480634
• ISSN: 00092673
• Web Site: https://academic.oup.com/bcsj/article-pdf/52/6/1701/56100801/bcsj.52.1701.pdf
• 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