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Facile Synthesis of Pyridines from Propargyl Amines: Concise Total Synthesis of Suaveoline Alkaloids
Author(s) -
Zhao Zhiwen,
Wei Hongbo,
Xiao Ke,
Cheng Bin,
Zhai Hongbin,
Li Yun
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201811812
Subject(s) - chemistry , propargyl , total synthesis , isomerization , alkyne , tandem , yield (engineering) , cascade reaction , pyridine , organic chemistry , combinatorial chemistry , catalysis , materials science , metallurgy , composite material
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.