An alternative synthesis and X-ray crystallographic confirmation of (−)-stepholidine. Issue 19 (11th May 2016)

• Record Type: Journal Article
• Authors: Gadhiya, Satishkumar V.; Hu, Chunhua; Harding, Wayne W.
• Is Part Of: Tetrahedron letters. Volume 57:Issue 19(2016)
• Page Start: 2090
• Page End: 2092
• Publication Date: 2016-05-11
• Subjects: Stepholidine -- THPB -- Tetrahydroprotoberberine -- Dopamine -- X-ray crystallography; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.03.108
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A new synthesis of a key lactone intermediate required for the synthesis of (−)-stepholidine (1 ) was achieved. (−)-Stepholidine was prepared in 23% overall yield in a fourteen-step synthetic sequence. The stereostructure of (−)-stepholidine prepared by this method was confirmed by single crystal X-ray diffraction. Abstract: A formal enantioselective synthesis of (−)-stepholidine that provides an alternative preparation of key lactone intermediate2 is described. The stereostructure of (−)-stepholidine prepared via this method was confirmed by X-ray diffraction.