Antiproliferating polyquinanes. VI.1) Synthesis of 2-methylene(3.3.3)propellan-3-one derivatives with hydrophilic groups

Kiyomi Kakiuchi, Masaki Ue, Teruhisa Nagashima, Masahiko Kinugawa, Kazuya Kobiro, Yoshito Tobe, Yoshinobu Odaira

Research output: Contribution to journalArticle

3 Scopus citations

Abstract

New analogues related to 2-methylenetricyclo[3.3.3.0]undecan-3-one (4), which shows potent antiproliferating activity, i.e., 2-(methoxymethoxy)-4-methylenetricyclo[3.3.3.0]undecan-3-one (5), (1S*,5R*,7S*)-7-(methoxymethoxy)- and hydroxy-2-methylenetricyclo[3.3.3.0]undecan-3-ones (6 and 7), and (1S*,5R*,8S*)-8-(methoxymethoxy)- and hydroxy-2-methylenetricyclo[3.3.3.0]-undecan-3-ones (8 and 9), were readily synthesized through skeletal transformations of derivatives of tricyclo [4.3.2.0]undecan-2-one (2).

Original languageEnglish
Pages (from-to)542-550
Number of pages9
JournalChemical and Pharmaceutical Bulletin
Volume36
Issue number2
DOIs
StatePublished - 1 Jan 1988

Keywords

  • [3.3.3]propellane
  • hydrophilic group
  • skeletal transformation
  • α-methylene cyclopentanone

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