Protecting-group-free total synthesis of (-)-rhazinilam and (-)-rhazinicine using a gold-catalyzed cascade cyclization

Kenji Sugimoto, Kazuki Toyoshima, Shiori Nonaka, Kenta Kotaki, Hirofumi Ueda, Hidetoshi Tokuyama

Research output: Contribution to journalArticlepeer-review

72 Citations (Scopus)

Abstract

'Rhaz'zmatazz: A total synthesis of (-)-rhazinilam and the first asymmetric total synthesis of (-)-rhazinicine were accomplished by using constructing the indolizinone core through the gold-catalyzed cyclization of a fully elaborated linear ynamide. The scope and generality of this cascade reaction for the construction of highly substituted indolizinones were also investigated.

Original languageEnglish
Pages (from-to)7168-7171
Number of pages4
JournalAngewandte Chemie - International Edition
Volume52
Issue number28
DOIs
Publication statusPublished - 2013 Jul 8

Keywords

  • alkaloids
  • cyclization
  • gold
  • natural products
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint

Dive into the research topics of 'Protecting-group-free total synthesis of (-)-rhazinilam and (-)-rhazinicine using a gold-catalyzed cascade cyclization'. Together they form a unique fingerprint.

Cite this