Facile Synthesis of Pyridines from Propargyl Amines: Concise Total Synthesis of Suaveoline Alkaloids

  • Angew Chem Int Ed Engl. 2019 Jan 21;58(4):1148-1152. doi: 10.1002/anie.201811812.
Zhiwen Zhao  1 ,  Hongbo Wei  1 ,  Ke Xiao  1 ,  Bin Cheng  1 ,  Hongbin Zhai  2 ,  Yun Li  1
Affiliations
  • 1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, China.
  • 2. Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen, 518055, China.
PMID: 30411835 DOI: 10.1002/anie.201811812
Abstract

A general and efficient protocol was developed for the synthesis of polysubstituted pyridines from propargyl amines and unsaturated carbonyl compounds through a tandem condensation/alkyne isomerization/6π 3-azatriene electrocyclization sequence. This process was found to be applicable to a wide range of readily available substrates (30 examples, up to 95 % yield) and could be readily performed on a preparative (20 g) scale. By taking advantage of this method for late-stage pyridine incorporation, we successfully completed the collective total synthesis of suveoline, norsuveoline, and macrophylline.

Keywords
6π electrocyclization; domino reactions; heterocycles; pyridine alkaloids; total synthesis.
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