Journal
ORGANIC LETTERS
Volume 8, Issue 22, Pages 5149-5152Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol062076r
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Funding
- NIGMS NIH HHS [R01 GM063150-02, R01 GM063150-01A1, GM 63150, R01 GM063150-05, R01 GM063150, R01 GM063150-04, R01 GM063150-03] Funding Source: Medline
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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.
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