ArticleOrganic letters2010
Synthesis of several cleistrioside and cleistetroside natural products via a divergent de novo asymmetric approach.
Article in Organic letters, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Review
- Synthetic efforts on the road to marine natural products bearing 4-RSC advances · 2021Review
- Recent advances in site-selective functionalization of carbohydrates mediated by organocatalysts.Carbohydrate research · 2019Review
- Achmatowicz Reaction and its Application in the Syntheses of Bioactive Molecules.RSC advances · 2016Article
- A Survey of Recent Synthetic Applications of 2,3-Dideoxy-Hex-2-enopyranosides.Molecules (Basel, Switzerland) · 2015Review
- Structure activity relationship study of Mezzettiasides natural products and their four new disaccharide analogues for anticancer/antibacterial activity.MedChemComm · 2014Article
- Article
- Synthesis of orthogonally protected bacterial, rare-sugar and D-glycosamine building blocks.Nature protocols · 2013Article
- 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
- Improving the affinity of SL0101 for RSK using structure-based design.ACS medicinal chemistry letters · 2012Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
The de novo asymmetric syntheses of several partially acylated dodecanyl tri- and tetra-rhamnoside natural products (cleistriosides-5 and 6 and cleistetrosides-2 to 7) have been achieved (19-24 steps). The divergent route requires the use of three or less protecting groups. The asymmetry was derived via Noyori reduction of an acylfuran. The rhamno-stereochemistry was installed by a diastereoselective palladium-catalyzed glycosylation, ketone reduction and dihydroxylation.
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Registered trials
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