Synlett 2016; 27(06): 876-879
DOI: 10.1055/s-0035-1561501
letter
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Synthesis of (–)-Pentazocine and (–)-Metazocine

Lin Hu
a  State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, 100083, P. R. of China   Email: zdszlh@bjmu.edu.cn
,
Lihe Zhang*
a  State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, 100083, P. R. of China   Email: zdszlh@bjmu.edu.cn
,
Hongbin Zhai*
a  State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, 100083, P. R. of China   Email: zdszlh@bjmu.edu.cn
b  Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology Department, Peking University, Shenzhen Graduate School, Shenzhen, 518055, P. R. of China   Email: zhaihb@pkusz.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 22 October 2015

Acccepted after revision: 22 November 2015

Publication Date:
05 January 2016 (online)


Abstract

We have accomplished an efficient asymmetric synthesis of (–)-pentazocine and (–)-metazocine from the readily available d-tyrosine, featuring a ring-closing metathesis (RCM) reaction for the formation of the C ring and an intramolecular Friedel–Crafts reaction for the assembly of the B ring. The new strategy established herein should be applicable to enantioselective synthesis of a broad range of chiral benzomorphan analogues, thereby facilitating the biological and medicinal chemistry studies of these clinically important molecules.

Supporting Information

 
  • References and Notes

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