PHOTOCATALYZED ADDITION OF ALCOHOLS TO 5-SUBSTITUTED 2,5-DIHYDROFURAN-2-ONES - NOVEL SYNTHESIS OF (3'R)-2',3'-DIDEOXY-3'-HYDROXYMETHYL NUCLEOSIDES

被引:33
作者
MANN, J
WEYMOUTHWILSON, AC
机构
[1] Department of Chemistry, Reading University, Reading RG6 2AD, Whiteknights
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 21期
关键词
D O I
10.1039/p19940003141
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Methanol and propan-2-ol add in a regiospecific and highly stereocontrolled fashion to 5-substituted 2.5-dihydrofuran-2-ones (butenolides) under irradiation. The photoadducts with methanol have been converted into a number of (3'R)-2',3'-dideoxy-3'-hydroxymethyl nucleosides.
引用
收藏
页码:3141 / 3148
页数:8
相关论文
共 12 条
[1]   SYNTHESIS AND ANTIVIRAL ACTIVITY OF 3'-DEOXY-3'-C-HYDROXYMETHYL NUCLEOSIDES [J].
BAMFORD, MJ ;
COE, PL ;
WALKER, RT .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2494-2501
[2]   CONJUGATE ADDITION OF METHANOL TO ALPHA-ENONES - PHOTOCHEMISTRY AND STEREOCHEMICAL DETAILS [J].
BENKO, Z ;
FRASERREID, B ;
MARIANO, PS ;
BECKWITH, ALJ .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (09) :2066-2072
[3]  
BUNDY GL, 1975, TETRAHEDRON LETT, P1957
[4]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[5]   SYNTHETIC APPLICATIONS OF PHOTOCHEMICALLY INDUCED ADDITION OF OXYCARBINYL SPECIES TO ALPHA-ENONES .2. ADDITION OF KETALS, ALDEHYDES, AND POLYFUNCTIONAL SPECIES [J].
FRASERREID, B ;
ANDERSON, RC ;
HICKS, DR ;
WALKER, DL .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (23) :3986-3995
[6]   SYNTHETIC APPLICATIONS OF PHOTOCHEMICALLY INDUCED ADDITION OF OXYCARBINYL SPECIES TO ALPHA-ENONES .1. ADDITION OF SIMPLE ALCOHOLS [J].
FRASERREID, B ;
HOLDER, NL ;
HICKS, DR ;
WALKER, DL .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (23) :3978-3985
[7]  
GILBERT A, 1991, ESSENTIALS MOL PHOTO, pCH5
[8]  
MANN J, 1992, SYNLETT, P67
[9]   A NEW APPROACH TO CIS-CHRYSANTHEMIC ACID [J].
MANN, J ;
WEYMOUTHWILSON, A .
CARBOHYDRATE RESEARCH, 1991, 216 :511-515
[10]   OXETANOCIN, A NOVEL NUCLEOSIDE FROM BACTERIA [J].
SHIMADA, N ;
HASEGAWA, S ;
HARADA, T ;
TOMISAWA, T ;
FUJII, A ;
TAKITA, T .
JOURNAL OF ANTIBIOTICS, 1986, 39 (11) :1623-1625