An approach to the narciclasine alkaloids via a quinone methide initiated cyclization reaction

被引:24
作者
Angle, SR
Wada, T
机构
[1] Department of Chemistry, University of California-Riverside, Riverside
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(97)10138-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereoselective synthesis of a possible intermediate for the synthesis of the narciclasine alkaloids from D-glucose is described. The key step of the sequence is a quinone methide initiated cyclization reaction, (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:7955 / 7958
页数:4
相关论文
共 29 条
[1]   A convenient approach to the aminocyclitol fragment of pancratistatin from 7-oxanorbornenes [J].
Acena, JL ;
Arjona, O ;
Iradier, F ;
Plumet, J .
TETRAHEDRON LETTERS, 1996, 37 (01) :105-106
[2]  
AHMED SI, 1997, HETEROCYCL COMMUN, V3, P135
[3]   FORMATION OF CARBON-CARBON BONDS VIA QUINONE METHIDE-INITIATED CYCLIZATION REACTIONS [J].
ANGLE, SR ;
ARNAIZ, DO ;
BOYCE, JP ;
FRUTOS, RP ;
LOUIE, MS ;
MATTSONARNAIZ, HL ;
RAINIER, JD ;
TURNBULL, KD ;
YANG, WJ .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6322-6337
[4]   QUINONE METHIDE INITIATED CYCLIZATION REACTIONS - STUDIES TOWARD THE SYNTHESIS OF (+)-PANCRATISTATIN [J].
ANGLE, SR ;
LOUIE, MS .
TETRAHEDRON LETTERS, 1993, 34 (30) :4751-4754
[5]   LYCORICIDINE AND PANCRATISTATIN ANALOGS FROM CYCLOPENTADIENE [J].
BANWELL, MG ;
COWDEN, CJ ;
GABLE, RW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (24) :3515-3518
[6]   NARCICLASINE - AN ANTIMITOTIC SUBSTANCE FROM NARCISSUS BULBS [J].
CERIOTTI, G .
NATURE, 1967, 213 (5076) :595-&
[7]  
CHAPLEUR Y, ANTIBIOTICS ANTIVIRA, P379
[8]   TOTAL SYNTHESIS OF (+/-)-PANCRATISTATIN [J].
DANISHEFSKY, S ;
LEE, JY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (13) :4829-4837
[9]   TOWARD (+)-PANCRATISTATIN - MODULATION OF MECHANISM IN AN INTRAMOLECULAR ELECTROPHILIC AROMATIC-SUBSTITUTION [J].
DOYLE, TJ ;
VANDERVEER, D ;
HASELTINE, J .
TETRAHEDRON LETTERS, 1995, 36 (35) :6197-6200
[10]   L-2-NITRO-1,3-ALKANEDIOLS BY STEREOSELECTIVE ADDITION OF NITROETHANOL TO ALDEHYDES - ON THE ASYMMETRIC ELECTROPHILIC ADDITION TO DOUBLE-BONDS [J].
EYER, M ;
SEEBACH, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (12) :3601-3606