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Beilstein J. Org. Chem. 2018, 14, 1595–1618, doi:10.3762/bjoc.14.137
Graphical Abstract
Figure 1: Design of potential antineoplastic nucleosides.
Scheme 1: Synthesis of 4’-thioDMDC.
Scheme 2: Synthesis of 4’-thioribonucleosides by Minakawa and Matsuda.
Scheme 3: Synthesis of 4’-thioribonucleosides by Yoshimura.
Figure 2: Concept of the Pummerer-type glycosylation and hypervalent iodine-mediated glycosylation.
Scheme 4: Oxidative glycosylation of 4-thioribose mediated by hypervalent iodine.
Figure 3: Speculated mechanism of oxidative glycosylation mediated by hypervalent iodine.
Scheme 5: Synthesis of purine 4’-thioribonucleosides using hypervalent iodine-mediated glycosylation.
Scheme 6: Unexpected glycosylation of a thietanose derivative.
Scheme 7: Speculated mechanism of the ring expansion of a thietanose derivative.
Scheme 8: Synthesis of thietanonucleosides using the Pummerer-type glycosylation.
Scheme 9: First synthesis of 4’-selenonucleosides.
Scheme 10: The Pummerer-type glycosylation of 4-selenoxide 74.
Scheme 11: Synthesis of purine 4’-selenonucleosides using hypervalent iodine-mediated glycosylation.
Figure 4: Concept of the oxidative coupling reaction applicable to the synthesis of carbocyclic nucleosides.
Scheme 12: Oxidative coupling reaction mediated by hypervalent iodine.
Scheme 13: Synthesis of cyclohexenyl nucleosides using an oxidative coupling reaction.
Figure 5: Concept of the oxidative coupling reaction of glycal derivatives.
Scheme 14: Oxidative coupling reaction of silylated uracil and DHP using hypervalent iodine.
Scheme 15: Proposed mechanism of the oxidative coupling reaction mediated by hypervalent iodine.
Figure 6: Synthesis of 2’,3’-unsaturated nucleosides using hypervalent iodine and a co-catalyst.
Scheme 16: Synthesis of dihydropyranonucleoside.
Scheme 17: Synthesis of acetoxyacetals using hypervalent iodine and addition of silylated base.
Scheme 18: One-pot fragmentation-nucleophilic additions mediated by hypervalent iodine.
Figure 7: The reaction of thioglycoside with hypervalent iodine in the presence of Lewis acids.
Scheme 19: Synthesis of disaccharides employing thioglycosides under an oxidative coupling reaction mediated b...
Scheme 20: Synthesis of disaccharides using disarmed thioglycosides by hypervalent iodine-mediated glycosylati...
Scheme 21: Glycosylation using aryl(trifluoroethyl)iodium triflimide.
Figure 8: Expected mechanism of hypervalent iodine-mediated glycosylation with glycals.
Scheme 22: Synthesis of oligosaccharides by hypervalent iodine-mediated glycosylation with glycals.
Scheme 23: Synthesis of 2-deoxy amino acid glycosides.
Figure 9: Rationale for the intramolecular migration of the amino acid unit.
Beilstein J. Org. Chem. 2007, 3, No. 37, doi:10.1186/1860-5397-3-37
Figure 1: Piclavines A1-A4.
Scheme 1: Enantiomeric enhancement by iterative AD.
Scheme 2: Asymmetric synthesis of indolidines 209D using an iterative AD.
Scheme 3: Asymmetric synthesis of piclavines A1 and A2 from (2R-[4S])-15.
Scheme 4: Asymmetric synthesis of piclavines A3 and A4 from (2R-[4R])-15.
Scheme 5: Asymmetric synthesis of enantiomers of piclavines (1–4).