Toward General Access to the <i>Aspidosperma</i>-Type Terpenoid Indole Alkaloids: Synthesis of the Key 3,3-Disubstituted Piperidones through Enantioselective Intramolecular Heck-Type Reaction of Chloroformamides

• Yasui Yoshizumi

  Graduate School of Pharmaceutical Sciences, Kyoto University

• Takeda Hiroshi

  Graduate School of Pharmaceutical Sciences, Kyoto University

• Takemoto Yoshiji

  Graduate School of Pharmaceutical Sciences, Kyoto University

Bibliographic Information

Other Title

• Toward general access to the Aspidosperma-type terpenoid indole alkaloids: synthesis of the key 3,3-disubstituted piperidones through enantioselective intramolecular heck-type reaction of chloroformamides

Abstract

An enantioselective intramolecular Heck-type reaction of chloroformamides has been developed for the synthesis of 3,3-disubstituted piperidones. The desired piperidone was formed in the presence of a palladium catalyst, an optically active phosphoramidite ligand, K₃PO₄ and Ag₃PO₄. The obtained piperidone was converted to epieburnamonine.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 56 (11), 1567-1574, 2008

  The Pharmaceutical Society of Japan

Keywords

• enantioselective reaction
• total synthesis
• terpenoid indole alkaloid

Details

• CRID: 1390001204171009536
• NII Article ID: 110006968058
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.56.1567
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 9685532
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I9685532
• Web Site: https://www.jstage.jst.go.jp/article/cpb/56/11/56_11_1567/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed