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Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Review Article

Diverse Approaches and Recent Advances in the Synthesis of Tetrahydroprotoberberines

Author(s): Satishkumar V. Gadhiya, Rajan Giri, Pierpaolo Cordone, Anupam Karki and Wayne W. Harding*

Volume 22 , Issue 19 , 2018

Page: [1893 - 1905] Pages: 13

DOI: 10.2174/1385272822666180906142624

Price: $65

Abstract

Racemic and enantioselective synthesis of tetrahydroprotoberberine (THPB) alkaloids, a family of natural products showing a wide range of biological activity, have been based either on extension or enhancement of conventional methods or on new, recently developed tactics. Classical approaches to synthesize the THPB scaffold have utilized Bischler-Napieralski cyclization/reduction or Pictet-Spengler reactions to generate a benzyltetrahydroisoquinoline motif, followed by Mannich type condensation to obtain the tetracyclic THPB core. In recent developments, contiguously tetra-substituted ring D moieties and chiral auxiliaries to install the chiral center have been utilized to synthesize THPBs. The present review summarizes various approaches adopted to synthesize THPBs and their congeners, based on the sequence of formation of rings B and C.

Keywords: THPB, tetrahydroprotoberberine, stepholidine, tetrahydropalmatine, chiral auxiliary, isocorypalmine, stylopine, govadine.

Graphical Abstract

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