ArticleOrganic letters2006
De novo asymmetric syntheses of SL0101 and its analogues via a palladium-catalyzed glycosylation.
Article in Organic letters, 2006. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed.
- Synthesis and biological study of the phomopsolide and phomopsolidone natural products.Chemical communications (Cambridge, England) · 2020Review
- Synthesis and Biological Evaluation of 4'-Substituted Kaempfer-3-ols.The Journal of organic chemistry · 2020Article
- The affinity of RSK for cylitol analogues of SL0101 is critically dependent on the B-ring C-4'-hydroxy.Chemical communications (Cambridge, England) · 2020Article
- Regioselective Synthesis of aOrganic letters · 2020Article
- Substrate-Controlled Direct α-Stereoselective Synthesis of Deoxyglycosides from Glycals Using B(CThe Journal of organic chemistry · 2019Article
- A Survey of Recent Synthetic Applications of 2,3-Dideoxy-Hex-2-enopyranosides.Molecules (Basel, Switzerland) · 2015Review
- Synthesis and Structure-Activity Relationship Study of 5a-Carbasugar Analogues of SL0101.ACS medicinal chemistry letters · 2015Article
- De novo synthesis and biological evaluation of C6″-substituted C4″-amide analogues of SL0101.Organic letters · 2014Article
- Article
- Synthesis of orthogonally protected bacterial, rare-sugar and D-glycosamine building blocks.Nature protocols · 2013Article
- The unusual mechanism of inhibition of the p90 ribosomal S6 kinase (RSK) by flavonol rhamnosides.Biochimica et biophysica acta · 2013Review
- Structure Activity Relationship Study of the Cleistriosides and Cleistetrosides for Antibacterial/Anticancer Activity.ACS medicinal chemistry letters · 2012Article
- Recent Advances in Transition Metal-Catalyzed Glycosylation.ACS catalysis · 2012Article
- De novo asymmetric synthesis of all-D-, all-L-, and D-/L-oligosaccharides using atom-less protecting groups.Journal of the American Chemical Society · 2012Article
- Analogs of the RSK inhibitor SL0101: optimization of in vitro biological stability.Bioorganic & medicinal chemistry letters · 2012Article
- Biosynthesis and Total Synthesis Studies on The Jadomycin Family of Natural Products.European journal of organic chemistry · 2012Article
- Improving the affinity of SL0101 for RSK using structure-based design.ACS medicinal chemistry letters · 2012Article
- De novo synthesis of natural products via the asymmetric hydration of polyenes.Chemical communications (Cambridge, England) · 2011Review
- Stereochemical survey of digitoxin monosaccharides: new anticancer analogues with enhanced apoptotic activity and growth inhibitory effect on human non-small cell lung cancer cell.ACS medicinal chemistry letters · 2011Article
- Synthesis of several cleistrioside and cleistetroside natural products via a divergent de novo asymmetric approach.Organic letters · 2010Article
Corrections and comments
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Authors and funding
2 authors.
Funding
Abstract
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]
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