Stereocontrolled Total Synthesis of (−)-Stemaphylline

Ana Varela, Lennart K B Garve, Daniele Leonori*, Varinder K. Aggarwal

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

36 Citations (Scopus)
431 Downloads (Pure)

Abstract

Homologation of readily available α-boryl pyrrolidines with metal carbenoids is especially challenging even when good leaving groups (Cl) are employed. By performing a solvent switch from Et2O to CHCl3, efficient 1,2-metalate rearrangement of the intermediate boronate occurs with both halide and ester leaving groups. The methodology was used in the total synthesis of the Stemona alkaloid (−)-stemaphylline in just 11 steps (longest linear sequence), with high stereocontrol (>20:1 d.r.) and 11 % overall yield. The synthesis also features a late-stage lithiation–borylation reaction with a tertiary amine containing carbenoid.

Original languageEnglish
Pages (from-to)2127-2131
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number8
Early online date18 Jan 2017
DOIs
Publication statusPublished - 6 Feb 2017

Keywords

  • boronic esters
  • lithiation–borylation
  • Stemona alkaloids
  • stereocontrol
  • total synthesis

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