Construction of AB-Ring System of Taxane Framework by A-Ring Annulation Strategy:Synthesis of 1-Hydroxy-8,11,11-trimethylbicyclo〔5.3.1〕undec-7-en-9-one by Way of Intramolecular Aldol Cyclization to Form the C1-C10 Bond

• YAMADA Koji

• IWADARE Hayato

• MUKAIYAMA Teruaki

書誌事項

タイトル別名

• Construction of AB-Ring System of Taxane Framework by A-Ring Annulation Strategy: Synthesis of 1-Hydroxy-8,11,11-trimethylbicyclo-(5.3.1)undec-7-en-9-one by Way of Intramolecular Aldol Cyclization to Form the C1-C10 Bond.
• Construction of AB-Ring System of Taxan

抄録

Construction of the AB-ring system of the taxane framework via an A-ring annulation strategy was demonstrated by base-mediated intramolecular aldol reaction of (Z)-2, 2-dimethyl-3-(1-methyl-2-oxopropylidene)cyclooctanone, affording the title compound, 1-hydroxy-8, 11, 11-trimethylbicyclo[5.3.1]undec-7-en-9-one. A cyclization precursor, the tetra-substituted (Z)-alkene, was prepared from the corresponding cyclooctanone derivative, 3-[(α, α-dimethylbenzyl)dimethylsiloxy]-2, 2-dimethylcyclooctanone via a bicyclic α, β-unsaturated lactone intermediate.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 45 (12), 1898-1905, 1997

  公益社団法人 日本薬学会

キーワード

• taxane AB-ring system
• A-ring annulation strategy
• intramolecular aldol reaction
• 1-hydroxy-8, 11, 11-trimethylbicyclo[5.3.1]undec-7-en-9-one
• tetra-substituted alkene
• bicyclic lactone

詳細情報

• CRID: 1390001204158873472
• NII論文ID: 110003662816
• NII論文ID: 130003773646
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.45.1898
• COI: 1:CAS:528:DyaK1cXltlOl
• ISSN: 13475223
• ISSN: 00092363
• NDL書誌ID: 4371054
• PubMed: 9433759
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I4371054
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/45/12/45_12_1898/_pdf
• 本文言語コード: en
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可