Synthesis of a cisplatin derivative from lithocholic acid. Issue 38 (20th September 2018)

• Record Type: Journal Article
• Authors: Hryniewicka, Agnieszka; Łotowski, Zenon; Seroka, Barbara; Witkowski, Stanisław; Morzycki, Jacek W.
• Is Part Of: Tetrahedron. Volume 74:Issue 38(2018)
• Page Start: 5392
• Page End: 5398
• Publication Date: 2018-09-20
• Subjects: Lithocholic acid -- l-Serine -- Diamines -- Cisplatin -- Platinum complexes; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.01.007
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A new steroidal-platinum(II) hybrid compound was synthesized using a simple and efficient methodology. The synthesis was performed by a convergent approach with cross metathesis (CM) as a key step. An olefin derived from lithocholic acid and a vinyl substituted ethylenediamine derived from l -serine were used as chiral building blocks, which were combined in the CM step. The most important advantage of this method was the utilization of l -serine as a cheap, stereoisomerically pure substrate. A steroid with a diamino system in the side chain was subjected to reaction with potassium tetrachloroplatinate to obtain the target platinum(II) complex. Attempts to synthesize similar diamine systems using the asymmetric Strecker reaction were unsuccessful. Graphical abstract: Image 1