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

被引：8

作者：

Cesario, Cara ^{[1
]}

Tardibono, Lawrence P., Jr. ^{[1
]}

Miller, Marvin J. ^{[1
]}

机构：

[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 23期

关键词：

ASYMMETRIC-SYNTHESIS; PROTEIN-SYNTHESIS; POLYOXIN-C; ANALOGS; INHIBITION; NUCLEOSIDES; TA; DIHYDROXYLATION; CYCLOPENTENES; PURINE;

D O I：

10.1016/j.tetlet.2010.04.006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：3053 / 3056

页数：4

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