Synthesis 2015; 47(10): 1399-1404
DOI: 10.1055/s-0034-1380137
paper
© Georg Thieme Verlag Stuttgart · New York

A Novel Asymmetric Synthesis of (+)-Deoxytylophorinine

Haining Lv
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China   Email: yushishan@imm.ac.cn
,
Song Xu
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China   Email: yushishan@imm.ac.cn
,
Shuanggang Ma
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China   Email: yushishan@imm.ac.cn
,
Yunbao Liu
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China   Email: yushishan@imm.ac.cn
,
Yong Li
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China   Email: yushishan@imm.ac.cn
,
Jing Qu
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China   Email: yushishan@imm.ac.cn
,
Shishan Yu*
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China   Email: yushishan@imm.ac.cn
› Author Affiliations
Further Information

Publication History

Received: 10 October 2014

Accepted after revision: 09 January 2015

Publication Date:
04 March 2015 (online)


Abstract

A novel asymmetric synthesis of a phenanthroindolizidine alkaloid, (+)-deoxytylophorinine, is reported, which uses a chiral nickel(II) complex of a glycine Schiff base to synthesize a substituted (R)-3-phenanthrylalanine as a key intermediate and Meldrum’s acid to construct the E ring.

Supporting Information