A 7-Step Formal Asymmetric Total Synthesis of Strictamine via an Asymmetric Propargylation and Metal-Mediated Cyclization

Myles W. Smith, Zhiyao Zhou, Alison X. Gao, Takuya Shimbayashi, Scott A. Snyder

Research output: Contribution to journalArticle

25 Scopus citations

Abstract

Herein is shown how a novel catalytic asymmetric propargylation of 3,4-dihydro-β-carboline, followed by a designed Au(I)/Ag(I)-mediated 6-endo-dig cyclization, can directly deliver the indolenine-fused methanoquinolizidine core of the akuammiline alkaloid strictamine in its native oxidation state, ultimately achieving a 7-step formal asymmetric total synthesis. Also demonstrated are how the cyclization products can rearrange into vincorine-type skeletons and a further use for the developed propargylation with the first catalytic asymmetric total synthesis of decarbomethoxydihydrogambirtannine.

Original languageEnglish (US)
Pages (from-to)1004-1007
Number of pages4
JournalOrganic Letters
Volume19
Issue number5
DOIs
StatePublished - Mar 3 2017
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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