ASYMMETRIC, STEREOCONTROLLED TOTAL SYNTHESIS OF (-)-BREVIANAMIDE-B

被引:152
作者
WILLIAMS, RM
GLINKA, T
KWAST, E
COFFMAN, H
STILLE, JK
机构
[1] Department of Chemistry, Colorado State University, Colorado, 80523, Fort Collins
关键词
D O I
10.1021/ja00158a048
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The asymmetric, stereocontrolled total synthesis of (-)-brevianamide B(2) is described. The synthesis features a stereocontrolled intramolecular SN2' cyclization to construct the central bicyclo[2.2.2] nucleus. A synthetic route to C-10-epibrevianamide A (49) is also described. A synthetic sample of a shunt metabolite (9) proposed by Birch in 1972 has been prepared and its oxidation chemistry in the context of the proposed biosynthetic schemes is discussed. © 1990, American Chemical Society. All rights reserved.
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页码:808 / 821
页数:14
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