Total Synthesis of (±)-Englerin A and Its Tuncated Analogues

Colleen Reagan, Graham Trevitt, Kirill Tchabanenko*

*Corresponding author for this work

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

A convergent approach allowed total synthesis of (±)-Englerin A, and its truncated analogues, employing a thermal 1,3-dipolar cycloaddition of a highly substituted pyrylium ylide with vinyl acetate as the key step. The key intermediate, a 8-oxabicyclo[3,2,1]octane oxygenated at the C6 position, was directly converted into a truncated Englerin A analogue. CuI catalyzed conjugate addition of vinyl Grignard to an enone, ozonolysis, and epimerisation of the resulting aldehyde allowed stereoselective introduction of the side-chain leading to a total synthesis of the racemic natural product. The developed chemistry will allow synthesis of more complex analogues of the natural product based on the use of the key bicyclo[3,2,1]octane scaffold.

Original languageEnglish
Pages (from-to)1027-1037
Number of pages11
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number5
Early online date25 Jan 2019
DOIs
Publication statusPublished - 01 Feb 2019

Keywords

  • 1,3-Dipolar cycloaddition
  • Englerin A
  • Synthetic strategy
  • Total synthesis
  • Truncated analogue

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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