Taxamycins: A new enediyne family with synthetic and biological potential

被引：26

作者：

Lu, YF ^{[1
]}

Harwig, CW ^{[1
]}

Fallis, AG ^{[1
]}

机构：

[1] UNIV OTTAWA,OTTAWA CARLETON CHEM INST,DEPT CHEM,OTTAWA,ON K1N 6N5,CANADA

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1995年 / 73卷 / 12期

关键词：

cancer; enediynes; synthesis; Pd(0) coupling;

D O I：

10.1139/v95-279

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Pd(0) based synthesis of two disilyl synthons (Z-1-trimethylsilyl-6-tert-butyldiphenylsilylhex 3-ene-1,5-diyne (18) and Z-1-trimethylsilyl-6-triisopropylsilylhex-3-ene 1,5-diyne (19)) and the selective removal of the trimethylsilyl group (K2CO3, MeOH) to afford 24 and 25 is described. These building blocks are employed in the construction of the taxamycin-12 compound 38 (16,17, 18-trimethyl-2-methyloxymethoxy-9-hydroxybicyclo[9.3.1]pentadec- 5-ene-3,7-diyne). The final ring closure to the 12-membered ring utilizes an intramolecular Cr-Ni mediated condensation of the iodoalkyne 37 (1,3,3-trimethyl-2-(2-oxoethyl)-4-(Z-1-methyloxymethoxy-7-iodohept-4-ene-2,6-diynyl)cyclohexene).

引用

页码：2253 / 2262

页数：10

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