Asymmetric syntheses of (-)-pentazocine and (-)-eptazocine through an aza-Prins cyclization

Qiang Chen; Xing Huo; Zhen Yang; Xuegong She

doi:10.1002/asia.201200505

Asymmetric syntheses of (-)-pentazocine and (-)-eptazocine through an aza-Prins cyclization

Chem Asian J. 2012 Nov;7(11):2543-6. doi: 10.1002/asia.201200505. Epub 2012 Aug 21.

Authors

Qiang Chen¹, Xing Huo, Zhen Yang, Xuegong She

Affiliation

¹ State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou 730000, PR China.

PMID: 22907930
DOI: 10.1002/asia.201200505

Abstract

Two down more to go: The asymmetric syntheses of (-)-pentazocine and (-)-eptazocine are presented. The highlights of the syntheses are the construction of the core skeleton through an aza-Prins cyclization and intramolecular Friedel-Crafts reaction.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aza Compounds / chemistry*
Crystallography, X-Ray
Cyclazocine / analogs & derivatives*
Cyclazocine / chemical synthesis
Cyclazocine / chemistry
Cyclization
Molecular Conformation
Pentazocine / chemical synthesis*
Pentazocine / chemistry
Stereoisomerism

Substances

Aza Compounds
eptazocine
Cyclazocine
Pentazocine