Application of ene-like reactions of aldehydes with vinyl ethers: Facile assembly of benzazocenone intermediates for mitomycinoids

被引:14
作者
Ciufolini, MA
Chen, MY
Lovett, DP
Deaton, MV
机构
[1] Department of Chemistry, MS 60, Rice University, Houston, TX 77005-1892
关键词
D O I
10.1016/S0040-4039(97)00933-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Benzazocenone intermediates for mitomycinoids are now available in only six steps. Key phases of this sequence include the ene-like reaction of 2-methoxypropene with a 2-azidophenyacetaldehyde and a novel heterocyclic ring formation/expansion reaction. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:4355 / 4358
页数:4
相关论文
共 16 条
[1]  
ARDAKANI MA, 1986, J CHEM SOC P1, P4139
[2]  
CIUFOLINI MA, 1996, ADV HETEROCYCLIC NAT, V3, pCH1
[3]  
CIUFOLINI MA, 1997, IN PRESS TETRAHEDRON, V53
[4]   A STEREOSPECIFIC ROUTE TO AZIRIDINOMITOSANES - THE SYNTHESIS OF NOVEL MITOMYCIN CONGENERS [J].
DANISHEFSKY, S ;
BERMAN, EM ;
CIUFOLINI, M ;
ETHEREDGE, SJ ;
SEGMULLER, BE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3891-3898
[5]   YB(FOD)3-PROMOTED ENE REACTION OF ALDEHYDES WITH VINYL ETHERS [J].
DEATON, MV ;
CIUFOLINI, MA .
TETRAHEDRON LETTERS, 1993, 34 (15) :2409-2412
[6]   TOTAL SYNTHESIS OF (+/-)-FR-900482 [J].
FUKUYAMA, T ;
XU, LH ;
GOTO, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (01) :383-385
[7]   TOTAL SYNTHESIS OF (+/-)-MITOMYCINS VIA ISOMITOMYCIN-A [J].
FUKUYAMA, T ;
YANG, LH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7881-7882
[8]  
KAOTH T, 1996, TETRAHEDRON LETT, V37, P3471
[9]   Total synthesis of natural (+)-FR900482 .3. Completion of the synthesis [J].
Katoh, T ;
Yoshino, T ;
Nagata, Y ;
Nakatani, S ;
Terashima, S .
TETRAHEDRON LETTERS, 1996, 37 (20) :3479-3482
[10]   TOTAL SYNTHESIS OF MITOMYCINS [J].
KISHI, Y .
JOURNAL OF NATURAL PRODUCTS, 1979, 42 (06) :549-568