Synthesis of Cyclopentanyl Carbocyclic 5-Fluorocytosine ((-)-5-Fluorocarbodine) Using a Facially Selective Hydrogenation Approach

被引：5

作者：

Cho, Jong Hyun ^{[1
,2
]}

Amblard, Franck ^{[1
,2
]}

Coats, Steven J. ^{[3
]}

Schinazi, Raymond F. ^{[1
,2
]}

机构：

[1] Emory Univ, Sch Med, Dept Pediat, Ctr AIDS Res,Lab Biochem Pharmacol, Decatur, GA 30033 USA

[2] Vet Affairs Med Ctr, Decatur, GA 30033 USA

[3] RFS Pharma LLC, Tucker, GA 30084 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 02期

关键词：

HEPATITIS-B-VIRUS; NUCLEOSIDE ANALOGS; BMS-200475; CYTOSINE; THYMINE; POTENT;

D O I：

10.1021/jo302038d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthetic route to biologically relevant (-)-5-fluorocarbodine 6 was developed. Direct coupling of N-6-protected 5-fluorouracil 15 with cyclopentenyl intermediate 13, followed by formation of a macrocycle between the base and the carbocyclic sugar moiety, via ring-closing metathesis, allowed for a facial selective hydrogenation of the sugar double bond to give, exclusively, the desired 4'-beta stereoisomer.

引用

页码：723 / 727

页数：5

共 35 条

[1] SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES [J].

AGROFOGLIO, L ;

SUHAS, E ;

FARESE, A ;

CONDOM, R ;

CHALLAND, SR ;

EARL, RA ;

GUEDJ, R .

TETRAHEDRON, 1994, 50 (36) :10611-10670

[2] Palladium-assisted routes to nucleosides [J].

Agrofoglio, LA ;

Gillaizeau, I ;

Saito, Y .

CHEMICAL REVIEWS, 2003, 103 (05) :1875-1916

[3] Metathesis strategy in nucleoside chemistry [J].

Amblard, F ;

Nolan, SP ;

Agrofoglio, LA .

TETRAHEDRON, 2005, 61 (30) :7067-7080

[4]

[Anonymous], 1986, JP GETTY MUSEUM J, VXIV, p[211, I]

[5]

[Anonymous], 1986, The J. Paul Getty, Museum Journal, VXIV, p[211, I], Patent No. [WO 02/32920 A2, 0232920]

[6] BMS-200475, a novel carbocyclic 2'-deoxyguanosine analog with potent and selective anti-hepatitis B virus activity in vitro [J].

Bisacchi, GS ;

Chao, ST ;

Bachard, C ;

Daris, JP ;

Innaimo, S ;

Jacobs, GA ;

Kocy, O ;

Lapointe, P ;

Martel, A ;

Merchant, Z ;

Slusarchyk, WA ;

Sundeen, JE ;

Young, MG ;

Colonno, R ;

Zahler, R .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (02) :127-132

[7] SYNTHESIS OF CHIRAL CARBOCYCLIC NUCLEOSIDES [J].

BORTHWICK, AD ;

BIGGADIKE, K .

TETRAHEDRON, 1992, 48 (04) :571-623

[8] Synthesis of cyclopentenyl carbocyclic nucleosides as potential antiviral agents against orthopoxviruses and SARS [J].

Cho, JH ;

Bernard, DL ;

Sidwell, RW ;

Kern, ER ;

Chu, CK .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (03) :1140-1148

[9]

Chu D., 2008, Carbocyclic compounds and methods for treating emerging diseases, including Influenza and Venezuela Equine Encephalitis virus, Patent No. [WO2008124157A1, 2008124157, WO 2008/124157 A1]

[10] THE BENZOYLATION OF URACIL AND THYMINE [J].

CRUICKSHANK, KA ;

JIRICNY, J ;

REESE, CB .

TETRAHEDRON LETTERS, 1984, 25 (06) :681-684

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