Synthesis of the 5′-Fluoro-2′β-methyl Analogues of Neplanocin

被引：9

作者：

Kumamoto, Hiroki ^{[1
]}

Kobayashi, Marina ^{[1
]}

Kato, Nobuyuki ^{[2
]}

Balzarini, Jan ^{[3
]}

Tanaka, Hiromichi ^{[1
]}

机构：

[1] Showa Univ, Sch Pharmaceut Sci, Shinagawa Ku, Tokyo 1428555, Japan

[2] Okayama Univ, Dept Mol Biol, Grad Sch Med Dent & Pharmaceut Sci, Okayama 7008558, Japan

[3] Katholieke Univ Leuven, Rega Inst Med Res, B-3000 Louvain, Belgium

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 14期

关键词：

Carbocycles; Nucleosides; Selenium; Electrophilic addition; Fluorine; S-ADENOSYLHOMOCYSTEINE HYDROLASE; EMPLOYING; (S; S)-HYDROBENZOIN; STEREOSELECTIVE-SYNTHESIS; BIOLOGICAL EVALUATION; MITSUNOBU; INHIBITOR; ACID;

D O I：

10.1002/ejoc.201100062

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of the 5'-fluoro-2'-beta-methyl analogues of neplanocin was carried out. Key intermediate cyclopentenone 19 was prepared from methyl alpha-D-mannopyranoside by a new approach consisting of ring-closing metathesis, stereoselective introduction of the 2'-methyl group, and intramolecular oxyselenenylation of the double bond as representative steps. Subsequent introduction of a fluorine atom at the 5'-position of 19 was performed by electrophilic fluorination by using Selectfluor.

引用

页码：2685 / 2691

页数：7

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