Stereochemical studies. XLIII. Novel reactivity of organometallic reagents to 5,5-ethylenedioxy-2-methyl-2-phenylcyclohexanone.

• 曽根 孝範

• 寺島 孜郎

• 山田 俊一

抄録

In connection with our studies on asymmetric synthesis of optically active diterpenes and steroids, introduction of a two carbon unit into the carbonyl group of 5, 5-ethylenedioxy-2-methyl-2-phenylcyclohexanone (1) was examined using several kinds of organometallic reagents as nucleophiles. Although N, N-dimethyl lithioacetamide (4f) could afford the desired 1, 2-addition product (8e), other organometallic reagents (4a-e) simply behaved as bases which cleaved the ketal ring of 1, giving the enol ether (5). Use of 4f-1, 4-diazabicyclo [2, 2, 2] octane complex could further improve the yield of 8e from 26% to 84%.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 24 (6), 1293-1298, 1976

  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: 1390282679149669504
• NII論文ID: 110003635132
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.24.1293
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/24/6/24_6_1293/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1977080590
• 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