biostudies-literatureShan MNIGMS NIH HHS5149-52https://www.ebi.ac.uk/biostudies/studies/S-EPMC2529254biostudies-literatureUnknown8(22)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. [reaction: see text]Organic lettersDe novo asymmetric syntheses of SL0101 and its analogues via a palladium-catalyzed glycosylation.PMC2529254R01 GM063150-02R01 GM063150-03R01 GM063150-01A1R01 GM063150R01 GM063150-04GM 63150R01 GM063150-05Shan MO'Doherty GAfalseDe novo asymmetric syntheses of SL0101 and its analogues via a palladium-catalyzed glycosylation.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. [reaction: see text]2006-01-01T00:00:00Z2006 Oct2024-10-18T13:54:19.307Z2019-03-27T00:16:28ZS-EPMC25292541704886510.1021/ol062076r