TiCl4 catalyzed cleavage of (25R)-22-oxo-23-spiroketals. Synthesis of sapogenins with furostanol and pyranone E rings on the side chain

Publication date: Available online 6 September 2019Source: SteroidsAuthor(s): Alejandro Corona-Díaz, J. Pablo García-Merinos, María E. Ochoa, Rosa E del Río, Rosa Santillan, Susana Rojas-Lima, Jacek W. Morzycki, Yliana LópezAbstractThe regioselective opening of the F ring of 22-oxo-23-spiroketals 7a-d using TiCl4 in acetic anhydride yielded the novel furostanols 11a-d along with cholestanic derivatives 8a-d with pyranone E ring. The structures of the new derivatives thus obtained were established using one- (DEPT) and two-dimensional 1H, 13C NMR experiments (COSY, HSQC, HMBC, NOESY). The 22α-hydroxyl orientation in compounds 11a-d was proposed by comparison of the 13C chemical shifts with those of other aglycone members of this family, and confirmed by combined NOESY and X-ray diffraction analysis of compound 11a.Graphical abstract
Source: Steroids - Category: Drugs & Pharmacology Source Type: research