Syntheses of carbocyclic aminonucleosides and (−)-epi-4′-carbocyclic puromycin: application of palladium(0)/indium iodide-allylations and tethered aminohydroxylations

✍ Scribed by Cara Cesario; Lawrence P. Tardibono Jr.; Marvin J. Miller

• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 351 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.04.006

✦ Synopsis

Carbocyclic aminonucleosides and epi-4'-carbocyclic puromycin were prepared from an acylnitroso-derived hetero Diels-Alder cycloadduct. Pd(0)/InI-mediated allylations of a formyl species were used to install the 4'-hydroxymethyl group. A tethered aminohydroxylation strategy was employed to install the cis-2',3'-aminoalcohol moiety with complete regio- and diastereocontrol.