Construction of Tricyclic Enone, a Common Precursor for Aphidicolane and Stemodane B/C/D-Ring System

• Tanaka Tetsuaki

  Graduate School of Pharmaceutical Sciences, Osaka University

• Yamamoto Sachiko

  Graduate School of Pharmaceutical Sciences, Osaka University

• Hiramatsu Kei

  Graduate School of Pharmaceutical Sciences, Osaka University

• Murakami Kazuo

  Graduate School of Pharmaceutical Sciences, Osaka University

• Yoshino Hitoshi

  Graduate School of Pharmaceutical Sciences, Osaka University

• Patra Debasis

  Graduate School of Pharmaceutical Sciences, Osaka University

• Iwata Chuzo

  Graduate School of Pharmaceutical Sciences, Osaka University

• Ohno Hiroaki

  Graduate School of Pharmaceutical Sciences, Osaka University

Abstract

Synthesis of a tricyclic enone (B/C/D ring system), a common key precursor for the aphidicolane- and stemodane-type diterpene, is described. The key reaction for the construction of the quaternary carbon center is allylation of epoxide at the more substituted carbon with an organotitanium reagent. Asymmetric reduction with DIP-Cl followed by stereoselective cyclization of spirocyclic ketone and the functional group modification gave the desired tricyclic enone in good yield.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 54 (8), 1138-1143, 2006

  The Pharmaceutical Society of Japan

Keywords

• aphidicolane
• stemodane
• allylation
• organotitanium reagent

Details

• CRID: 1390001204171278848
• NII Article ID: 110004847232
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.54.1138
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 7991489
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I7991489
• Web Site: https://www.jstage.jst.go.jp/article/cpb/54/8/54_8_1138/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed