Syntheses of C2′-Fluorinated Analogs of Solamin

• Kojima Naoto

  Kyoto Pharmaceutical University

• Hayashi Hiromi

  Graduate School of Pharmaceutical Sciences, Osaka University

• Iwasaki Hiroki

  Kyoto Pharmaceutical University

• Yamashita Masayuki

  Kyoto Pharmaceutical University

Bibliographic Information

Other Title

• Syntheses of C2'-Fluorinated Analogs of Solamin

Abstract

The details of the total syntheses of C2′-fluorinated analogs of solamin, an antitumor annonaceous acetogenin, are described. Fluorine was enantioselectively introduced at the C2′-position by organocatalytic α-fluorination of the aldehyde according to a previously reported method. C2′-fluorinated solamin and its C2′-diastereomer were synthesized by the Sonogashira coupling of a tetrahydrofuran fragment and fluorine-containing γ-lactone fragments.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 68 (7), 675-678, 2020-07-01

  The Pharmaceutical Society of Japan

Keywords

• annonaceous acetogenin
• fluorinated analog
• antitumor agent
• convergent synthesis

Details

• CRID: 1390566775147914112
• NII Article ID: 130007867293
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.c20-00223
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 030485470
• PubMed: 32612003
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I030485470
• Web Site: https://www.jstage.jst.go.jp/article/cpb/68/7/68_c20-00223/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/2021139594
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed