Concise Asymmetric Total Synthesis of ent-Ancistrocladinium A

Kyung Hee Kim, Cheol-Hong Cheon

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

An asymmetric total synthesis of ent-ancistrocladinium A was developed via chiral phosphoric acid-catalyzed asymmetric reductive amination of 1-aryl-2-propanone and naphthylamine followed by a Bischler–Napieralski reaction. Direct use of the naphthyl moiety in the amine as a key building block in the natural product allowed us to achieve the total synthesis of ancistrocladinium A in only three steps from the known starting materials. (Figure presented.).

Original languageEnglish
Pages (from-to)2883-2888
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume358
Issue number18
DOIs
Publication statusPublished - 2016 Sep 15

    Fingerprint

Keywords

  • ancistrocladinium A
  • chiral phosphoric acid catalysis
  • naphthylisoquinoline alkaloids
  • reductive amination
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this