A short and efficient route to novel scyphostatin analogues

被引:46
作者
Runcie, KA [1 ]
Taylor, RJK [1 ]
机构
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
关键词
D O I
10.1021/ol0164132
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Several novel scyphostatin analogues have been prepared in up to 18% yield over five steps from commercially available 4-bromogualacol, utilizing an organometallic addition to afford the desired syn-hydroxy-epoxides.
引用
收藏
页码:3237 / 3239
页数:3
相关论文
共 15 条
[1]   Synthetic approaches to the manumycin A, B and C antibiotics: The first total synthesis of (+)-manumycin A [J].
Alcaraz, L ;
Macdonald, G ;
Ragot, J ;
Lewis, NJ ;
Taylor, RJK .
TETRAHEDRON, 1999, 55 (12) :3707-3716
[2]  
ARNEZ C, 2001, CHEMBIOCHEM, P141
[3]  
Gao SY, 2000, SYNLETT, P421
[4]   Acetal and ketal deprotection using montmorillonite K10: The first synthesis of syn-4,8-dioxatricyclo[5.1.0.0(3,5)]-2,6-octanedione [J].
Gautier, ECL ;
Graham, AE ;
McKillop, A ;
Standen, SP ;
Taylor, RJK .
TETRAHEDRON LETTERS, 1997, 38 (11) :1881-1884
[5]  
Genski T, 1999, SYNLETT, P795
[6]  
Gurjar MK, 2000, HETEROCYCLES, V53, P1885
[7]   Synthesis (and alternative proof of configuration) of the scyphostatin C(1′)-C(20′) trienoyl fragment [J].
Hoye, TR ;
Tennakoon, MA .
ORGANIC LETTERS, 2000, 2 (10) :1481-1483
[8]   Enantiocontrolled synthesis of (4S,5S,6S)-6-benzyl-4,5-epoxy-6-hydroxy-2-cyclohexen-1-one, a model compound for the epoxycyclohexenone moiety of scyphostatin [J].
Izuhara, T ;
Katoh, T .
TETRAHEDRON LETTERS, 2000, 41 (40) :7651-7655
[9]   Studies toward the total synthesis of scyphostatin: First entry to the highly functionalized cyclohexenone segment [J].
Izuhara, T ;
Katoh, T .
ORGANIC LETTERS, 2001, 3 (11) :1653-1656
[10]   THE SPHINGOMYELIN PATHWAY IN TUMOR-NECROSIS-FACTOR AND INTERLEUKIN-1 SIGNALING [J].
KOLESNICK, R ;
GOLDE, DW .
CELL, 1994, 77 (03) :325-328