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

24 Citations (Scopus)

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

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Cyclization
Metals
Carbolines
alkaloids
synthesis
musculoskeletal system
Alkaloids
Skeleton
metals
Oxidation
oxidation
products
strictamine
vincorine

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

A 7-Step Formal Asymmetric Total Synthesis of Strictamine via an Asymmetric Propargylation and Metal-Mediated Cyclization. / Smith, Myles W.; Zhou, Zhiyao; Gao, Alison X.; Shimbayashi, Takuya; Snyder, Scott A.

In: Organic Letters, Vol. 19, No. 5, 03.03.2017, p. 1004-1007.

Research output: Contribution to journalArticle

Smith, Myles W. ; Zhou, Zhiyao ; Gao, Alison X. ; Shimbayashi, Takuya ; Snyder, Scott A. / A 7-Step Formal Asymmetric Total Synthesis of Strictamine via an Asymmetric Propargylation and Metal-Mediated Cyclization. In: Organic Letters. 2017 ; Vol. 19, No. 5. pp. 1004-1007.
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