Total synthesis of pyrano[3,2-e] indole alkaloid fontanesine B by a double cyclization strategy

Tomoki Itoh, Yuusuke Chiba, Shunsuke Kawaguchi, Yuki Koitaya, Yuuma Yoneta, Koji Yamada, Takumi Abe

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

The regioselective synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by two different cyclizations is described. The complete regioselectivity is controlled by the C4 Pictet-Spengler cyclization, in which an iminium ion acts as a transient directing (TDG) group. Furthermore, carbolines were constructed by a new Bischler-Napieralski-type cyclization, in which an unprecedented trichloromethyl carbamate serves as a reactive group.

Original languageEnglish
Pages (from-to)10420-10424
Number of pages5
JournalRSC Advances
Volume9
Issue number18
DOIs
Publication statusPublished - 2019
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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