Quick Access to Pyridines through 6π-3-Azatriene Electrocyclization: Concise Total Synthesis of Suaveoline Alkaloids

Hongbo Wei; Yun Li

doi:10.1055/s-0037-1611811

Synlett, Table of Contents

Synlett 2019; 30(14): 1615-1620
DOI: 10.1055/s-0037-1611811

synpacts

Quick Access to Pyridines through 6π-3-Azatriene Electrocyclization: Concise Total Synthesis of Suaveoline Alkaloids

Hongbo Wei

^aShaanxi Key Laboratory of Natural Products and Chemical Biology College of Chemistry and Pharmacy, Northwest A&F University 22 Xinong Road, Yangling 712100, P. R. of China

,

Yun Li *

^bState Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. of China Email: liyun@lzu.edu.cn

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Abstract

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This paper is dedicated to the Lanzhou University on the occasion of its 110^th anniversary.

Abstract

Pyridine is a prevalent structural heterocyclic motifs in natural products, pharmaceuticals, and advanced materials. Several different methodologies have been developed for the synthesis of these kinds of molecules. However, a sustainable and efficient procedure for the synthesis of pyridines is still highly desirable. In this Synpacts article, we highlight our recent approach to the construction of highly substituted pyridines though a tandem condensation/alkyne isomerization/6π-3-azatriene electrocyclization sequence. The present protocol was used to synthesize a series of polysubstituted pyridines (30 examples) in moderate to good yields. The process also permitted the development of a concise strategy for collective total syntheses of suaveoline, norsuaveoline, and macrophylline.

Key words

pyridines - alkaloids - 6π-electrocyclization - total synthesis - tandem reaction

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References

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