A Convenient and Stereoselective Synthesis of 11Z-3,4-Didehydroretinal by Horner-Emmons Reaction Using Diphenyl Phosphonate

• Wada Akimori

  Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University

• Wang Fei

  Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University

• Ito Masayoshi

  Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University

抄録

A convenient synthesis of 3,4-didehydroretinal was developed. The Horner–Emmons reaction between 3,4-didehydro-β-ionone and diphenyl phosphonate in the presence of crown ether gave the retinonitrile as an isomeric mixture, in which the newly produced double bond was predominantly 11Z-form. After separation of the 11Z-form retinonitrile, it was converted into the corresponding retinal in good yield without isomerization of the double bonds.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 56 (1), 112-114, 2008

  公益社団法人 日本薬学会

キーワード

• visual pigment
• 11<i>Z</i>-3,4-didehydroretinal
• diphenyl phosphonate
• Horner–Emmons reaction
• <i>Z</i>-selectivity

詳細情報

• CRID: 1390001204168472320
• NII論文ID: 110006531704
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.56.112
• ISSN: 13475223
• ISSN: 00092363
• ISSN: http://id.crossref.org/issn/00092363
• NDL書誌ID: 9313581
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I9313581
• Web Site: http://www.jstage.jst.go.jp/article/cpb/56/1/56_1_112/_pdf
• 本文言語コード: en
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可