SYNTHESIS AND OXIDATIVE ACTIVATION OF AN OXABICYCLO[7.2.1] ENEDIYNE

被引:33
作者
BRANDSTETTER, T [1 ]
MAIER, ME [1 ]
机构
[1] UNIV KONSTANZ,FAK CHEM,D-78434 CONSTANCE,GERMANY
关键词
D O I
10.1016/S0040-4020(01)80628-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxabicyclo[7.2.1] enediyne 23 which contains an ortho-methoxybenzyl group at the anomeric position was synthesized from methyl-2,3-anhydro-alpha-D-lyxofuranoside (7). Treatment of this stable bicyclic enediyne with ceric ammonium nitrate at room temperature in CH3CN/H2O gave the aromatized monocyclic compound 25.
引用
收藏
页码:1435 / 1448
页数:14
相关论文
共 63 条
[1]   TOTAL SYNTHESIS OF HALICHONDRIN-B AND NORHALICHONDRIN-B [J].
AICHER, TD ;
BUSZEK, KR ;
FANG, FG ;
FORSYTH, CJ ;
JUNG, SH ;
KISHI, Y ;
MATELICH, MC ;
SCOLA, PM ;
SPERO, DM ;
YOON, SK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (08) :3162-3164
[2]  
AUDRAIN H, 1993, SYNLETT, P20
[3]   REACTIVE 1,4-DEHYDROAROMATICS [J].
BERGMAN, RG .
ACCOUNTS OF CHEMICAL RESEARCH, 1973, 6 (01) :25-31
[4]   PYRENOLINE-A AND PYRENOLINE-B, 2 NEW PHYTOTOXINS FROM PYRENOPHORA-TERES [J].
COVAL, SJ ;
HRADIL, CM ;
LU, HSM ;
CLARDY, J ;
SATOURI, S ;
STROBEL, GA .
TETRAHEDRON LETTERS, 1990, 31 (15) :2117-2120
[5]   THE ESPERAMICIN-CALICHEAMICIN AGLYCONES - RING-CLOSURE OF A SIMPLE STRAINED SYSTEM MEDIATED BY CHROMIUM(II)-NICKEL(II) SALTS [J].
CREVISY, C ;
BEAU, JM .
TETRAHEDRON LETTERS, 1991, 32 (27) :3171-3174
[6]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156
[7]   3-DEOXY-2,5-DI-ORTHO-PARA-NITROBENZOYL-ALPHA-D-THREO-PENTOFURANOSYL BROMIDE, A STARTING MATERIAL FOR SYNTHESIS OF NUCLEOSIDES [J].
ELKHADEM, HS ;
AUDICHYA, TD ;
WITHEE, MJ .
CARBOHYDRATE RESEARCH, 1974, 33 (02) :329-337
[8]  
ELKHADEM HS, 1978, NUCL ACID CHEM 1, P169
[9]  
FUJIMOTO Y, 1986, CHEM PHARM BULL, V34, P1497
[10]   MECHANISM OF NEOCARZINOSTATIN ACTION - ROLE OF DNA MICROSTRUCTURE IN DETERMINATION OF CHEMISTRY OF BISTRANDED OXIDATIVE DAMAGE [J].
GOLDBERG, IH .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (07) :191-198