Synthesis of (+)-Tacamonine via Stereoselective Radical Cyclization

Myles W. Smith, Jasmin Ferreira, Roger Hunter, Gerhard A. Venter, Hong Su

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

A concise, asymmetric synthesis of the indole alkaloid (+)-tacamonine is reported involving a stereoselective radical cyclization of a 1-phenylsulfanyl tetrahydro-β-carboline bearing a pendant enoate ester side chain as a key step. In this process, a single stereocenter in the side chain allows for the formation of two stereocenters of the natural product in a highly diastereoselective fashion. Computational investigations of this key cyclization support the experimentally observed outcome and shed light on the factors impacting its stereoselectivity.

Original languageEnglish (US)
Pages (from-to)8740-8745
Number of pages6
JournalOrganic Letters
Volume21
Issue number21
DOIs
StatePublished - Nov 1 2019
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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