Synthesis 2017; 49(16): 3731-3739
DOI: 10.1055/s-0036-1588818
paper
© Georg Thieme Verlag Stuttgart · New York

Catalyst-Free Intramolecular 1,3-Dipolar Cycloaddition of Ethyl (2-Formylphenyl) Vinylphosphonates: A Highly Stereoselective Access to Phosphadihydrocoumarin-Fused Pyrrolizidines/Pyrrolidines

Jie Jiang
a   Key Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, Hainan Province, P. R. of China
,
Mingshu Wu*
a   Key Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, Hainan Province, P. R. of China
,
Zhongxiang Zhu
a   Key Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, Hainan Province, P. R. of China
,
Dulin Kong
b   School of Pharmaceutical Sciences, Hainan Medical University, Haikou 571199, Hainan Province, P. R. of China   Email: wmsh@hainnu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 01 December 2016

Accepted after revision: 31 March 2017

Publication Date:
08 May 2017 (online)


Abstract

Pyrrolizidine and coumarins both have biological activities, and their molecular skeletons are commonly found in several biomolecules and drug molecules. We have developed a catalyst-free, intramolecular 1,3-dipolar cycloaddition to synthesize phosphadihydrocoumarin-fused pyrrolizidine/pyrrolidine scaffolds with high stereoselectivity.

Supporting Information