A Unified Strategy to Fluorinated Nucleoside Analogues Via an Electrophilic Manifold

被引：5

作者：

Neel, Andrew J. ^{[1
]}

Turnbull, Ben W. H. ^{[1
]}

Carson, William P. ^{[1
]}

Benkovics, Tamas ^{[1
]}

Chung, Cheol K. ^{[1
]}

Johnson, Heather C. ^{[1
]}

Liu, Zhuqing ^{[1
]}

Peng, Feng ^{[1
]}

Rummelt, Stephan M. ^{[1
]}

Song, Zhiguo Jake ^{[1
]}

Tan, Lushi ^{[1
]}

Wang, Lu ^{[1
]}

Xu, Feng ^{[1
]}

机构：

[1] Merck & Co Inc, Proc Res & Dev, Rahway, NJ 07065 USA

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 41期

关键词：

ACID RELATED-COMPOUNDS; DERIVATIVES; PURINE; ANTICANCER; REAGENTS; SHIFT;

D O I：

10.1021/acs.orglett.2c03367

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we present a strategy for the preparation of 3'-fluorinated nucleoside analogues via the aminocatalytic, electrophilic fluorination of readily accessible and bench-stable 2'-ketonucleosides. Initially developed to facilitate the manufacture of 3'-fluoroguanosine (3'-FG)-a substructure of anticancer therapeutic MK-1454-this strategy has been extended to the synthesis of a variety of 3'-fluoronucleosides. Finally, we demonstrate the utility of the 2'-ketonucleoside synthon as a platform for further diversification and suggest that this methodology should be broadly applicable to the discovery of novel nucleoside analogues.

引用

页码：7701 / 7706

页数：6

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