Synlett 2015; 26(07): 921-926
DOI: 10.1055/s-0034-1380172
letter
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of Two Pyrrole Spiroketal Alkaloids: Pollenopyrroside A and Capparisine B

Zhi Cao
School of Pharmaceutical Science and Technology, State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, P. R. of China   eMail: zyzhao@dlut.edu.cn
,
Yueqing Li
School of Pharmaceutical Science and Technology, State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, P. R. of China   eMail: zyzhao@dlut.edu.cn
,
Shisheng Wang
School of Pharmaceutical Science and Technology, State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, P. R. of China   eMail: zyzhao@dlut.edu.cn
,
Xiuhan Guo
School of Pharmaceutical Science and Technology, State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, P. R. of China   eMail: zyzhao@dlut.edu.cn
,
Liu Wang
School of Pharmaceutical Science and Technology, State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, P. R. of China   eMail: zyzhao@dlut.edu.cn
,
Weijie Zhao*
School of Pharmaceutical Science and Technology, State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, P. R. of China   eMail: zyzhao@dlut.edu.cn
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Publikationsverlauf

Received: 25. November 2014

Accepted after revision: 12. Januar 2015

Publikationsdatum:
10. Februar 2015 (online)


Abstract

Pollenopyrroside A and capparisine B, two diastereoisomers of pyrrole spiroketal alkaloids isolated from Brassica campestris pollen and Capparis spinosa, were synthesized by an improved microwave-­assisted bishydroxymethylation of pyrrole and acid-catalyzed spirocyclization as key steps with total yields of 2.7 and 8.8%, respectively.

Supporting Information