An alternative synthesis and x-ray crystallographic confirmation of (-)-stepholidine

Satishkumar V Gadhiya; Chunhua Hu; Wayne W Harding

doi:10.1016/j.tetlet.2016.03.108

An alternative synthesis and x-ray crystallographic confirmation of (-)-stepholidine

Tetrahedron Lett. 2016 May 11;57(19):2090-2092. doi: 10.1016/j.tetlet.2016.03.108.

Authors

Satishkumar V Gadhiya¹, Chunhua Hu², Wayne W Harding³

Affiliations

¹ Department of Chemistry, Hunter College, City University of New York, 695 Park Avenue, New York 10065, USA; Ph.D. Program in Chemistry, The Graduate Center of The City University of New York, 365 5th Avenue, New York 10016, USA.
² Molecular Design Institute, Department of Chemistry, New York University, 100 Washington Square, New York 10003, USA.
³ Department of Chemistry, Hunter College, City University of New York, 695 Park Avenue, New York 10065, USA; Ph.D. Program in Chemistry, The Graduate Center of The City University of New York, 365 5th Avenue, New York 10016, USA; Ph.D. Program in Biochemistry, The Graduate Center of The City University of New York, 365 5th Avenue, New York 10016, USA.

Abstract

A formal enantioselective synthesis of (-)-stepholidine that provides an alternative preparation of key lactone intermediate 2 is described. The stereostructure of (-)-stepholidine prepared via this method was confirmed by x-ray diffraction.

Keywords: Dopamine; Stepholidine; THPB; Tetrahydroprotoberberine; X-ray crystallography.

Abstract

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