Synlett 2014; 25(16): 2260-2264
DOI: 10.1055/s-0034-1378897
cluster
© Georg Thieme Verlag Stuttgart · New York

Tandem Diels–Alder [4+2] Cycloadditions and Intramolecular [3+2] Cross-Cycloadditions of Dienylcyclopropane 1,1-Diesters

Jun Ren
State Key Laboratory and Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, 94 Weijin Road, Tianjin 300071, P. R. of China   Email: wzwrj@nankai.edu.cn
,
Jilai Bao
State Key Laboratory and Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, 94 Weijin Road, Tianjin 300071, P. R. of China   Email: wzwrj@nankai.edu.cn
,
Weiwei Ma
State Key Laboratory and Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, 94 Weijin Road, Tianjin 300071, P. R. of China   Email: wzwrj@nankai.edu.cn
,
Zhongwen Wang*
State Key Laboratory and Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, 94 Weijin Road, Tianjin 300071, P. R. of China   Email: wzwrj@nankai.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 12 May 2014

Accepted after revision: 30 July 2014

Publication Date:
09 September 2014 (online)


Preview

Abstract

A novel tandem reaction by combination of Diels–Alder [4+2] cycloaddition and [3+2] IMCC (intramolecular cross-cyclo­addition) of dienylcyclopropane 1,1-diesters has been successfully developed. In this reaction, three new rings and four new stereocenters were generated in one-pot. This supplies a strategy for rapid construction of 6,6- and 6,7-fused carbocyclic skeletons which are common cores in many biologically important natural products.

Supporting Information