910041-19-9Relevant articles and documents
Regioselective Synthesis of a C-4′′ Carbamate, C-6′′ n-Pr Substituted Cyclitol Analogue of SL0101
Fukuda, Shinji,Lannigan, Deborah A.,Li, Mingzong,Li, Yu,O'Doherty, George A.,Sandusky, Zachary M.,Vemula, Rajender,Wu, Bulan,Zhang, Qi
, p. 1448 - 1452 (2020/03/13)
An asymmetric synthesis of two analogues of SL0101 (1) has been achieved. The effort is aimed at the discovery of inhibitors of the p90 ribosomal S6 kinase (RSK) with improved bioavailability. The route relies upon the use of the Taylor catalyst to regios
De novo asymmetric syntheses of SL0101 and its analogues via a palladium-catalyzed glycosylation
Shan, Mingde,O'Doherty, George A.
, p. 5149 - 5152 (2007/10/03)
(Chemical Equation Presented) The enantioselective syntheses of naturally occurring kaempferol glycoside SL0101 (1a) and its analogues 1b-e, as well as their enantiomers, have been achieved in 7-10 steps. The routes rely upon a diastereoselective palladium-catalyzed glycosylation, ketone reduction, and dihydroxylation to introduce the rhamno-stereochemistry. The asymmetry of the sugar moiety of these kaempferol glycosides was derived from Noyori reduction of an acylfuran. An acetyl group shift from an axial (C-2) to equatorial position (C-3) under basic conditions was also described.