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- Title
Facile Synthesis of Pyridines from Propargyl Amines: Concise Total Synthesis of Suaveoline Alkaloids.
- Authors
Zhao, Zhiwen; Wei, Hongbo; Xiao, Ke; Cheng, Bin; Zhai, Hongbin; Li, Yun
- 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.
- Subjects
PYRIDINE synthesis; AMINES; ALKALOID synthesis; RING formation (Chemistry); ELECTROCYCLIC reactions (Chemistry); ISOMERIZATION
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 4, p1160
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201811812