Total Synthesis of the Epimer at C-6′ of the Miharamycin B Framework

被引：8

作者：

Marcelo, Filipa ^{[1
,3
]}

Abou-Jneid, Robert ^{[3
]}

Sollogoub, Matthieu ^{[3
]}

Marrot, Jerome ^{[2
]}

Rauter, Amelia P. ^{[1
]}

Bleriot, Yves ^{[3
]}

机构：

[1] Univ Lisbon, Fac Ciencias, Dept Quim & Bioquim, Carbohydrate Chem Grp,CQB FCUL, P-1749016 Lisbon, Portugal

[2] Univ Versailles St Quentin, Inst Lavoisier, UMR 8180, F-78035 Versailles, France

[3] UPMC Univ Paris 06, Equipe Glycochim, Inst Parisien Chim Mol, UMR 7201, F-75005 Paris, France

来源：

SYNLETT | 2009年 / 08期

关键词：

antibiotics; natural products; nucleosides; total synthesis; AMIPURIMYCIN; MOIETY;

D O I：

10.1055/s-0029-1216733

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of the epimer at C-6' of the core of the complex nucleoside antibiotic miharamycin B is reported. Optimization of the N-glycosylation key step involving the atypical 2-aminopurine nucleobase and a bicyclic glycosyl donor enabled to access the N-9-nucleoside in reasonable yield which was further decorated. The stereochemistry at C-6' has been secured by X-ray crystallography.

引用

页码：1269 / 1272

页数：4

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