Synthesis of Octahydro- and Decahydroquinolines by a One-Pot Cascade Reaction of Tetrasubstituted Enecarbamate

• Kurose, Tomohiro

  Graduate School of Pharmaceutical Sciences, Kyoto University

• Tsukano, Chihiro

  Graduate School of Pharmaceutical Sciences, Kyoto University

• Takemoto, Yoshiji

  Graduate School of Pharmaceutical Sciences, Kyoto University

Abstract

A transition-metal-catalyzed cyclopropanation followed by ring opening was investigated for the synthesis of octahydroquinolines 4 and decahydroquinolines 5 having a quaternary carbon center at the angular position, which are core structures of the fawcettimine-type alkaloids. A tandem reaction was also established for the synthesis of decahydroquinolines 5 and the tricyclic compound 6 through an iminium ion intermediate, readily produced by acidic treatment of cyclopropane 2.

Journal

• Organic Letters

  Organic Letters 19 (18), 4762-4765, 2017-09-15

  American Chemical Society

Keywords

• Organic Chemistry
• Physical and Theoretical Chemistry
• Biochemistry

Details

• CRID: 1050282813185877120
• NII Article ID: 120006547383
• ISSN: 15237060
• ISSN: 15237052
• DOI: 10.1021/acs.orglett.7b02122
• HANDLE: 2433/235944
• Web Site: https://pubs.acs.org/doi/pdf/10.1021/acs.orglett.7b02122
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • Crossref
  • CiNii Articles
  • KAKEN