Diverse Approaches and Recent Advances in the Synthesis of Tetrahydroprotoberberines

Title:Diverse Approaches and Recent Advances in the Synthesis of Tetrahydroprotoberberines

Volume: 22 Issue: 19

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

Affiliation:

• Department of Chemistry, Hunter College, City University of New York, 695 Park Avenue, New York 10065, NY,United States

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

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.

Cite this article as:

Gadhiya V. Satishkumar, Giri Rajan, Cordone Pierpaolo, Karki Anupam and Harding W. Wayne*, Diverse Approaches and Recent Advances in the Synthesis of Tetrahydroprotoberberines, Current Organic Chemistry 2018; 22 (19) . https://dx.doi.org/10.2174/1385272822666180906142624