SYNTHESIS OF HELICALLY CHIRAL MOLECULES - STEREOSELECTIVE TOTAL SYNTHESIS OF THE PERYLENEQUINONES PHLEICHROME AND CALPHOSTIN-A
SYNTHESIS OF HELICALLY CHIRAL MOLECULES - STEREOSELECTIVE TOTAL SYNTHESIS OF THE PERYLENEQUINONES PHLEICHROME AND CALPHOSTIN-A
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DOI：
10.1021/ja00149a012
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发表时间：
1995-11-08
影响因子：
15
通讯作者：
GRANT, EB
中科院分区：
文献类型：
--
作者：
COLEMAN, RS;GRANT, EB
详细介绍了苝醌类天然产物脉色素和钙磷素A的全合成方法。这些合成基于（1）从头构建区域特异性氧化和选择性保护的萘亚基，（2）使用手性（α-烷氧基烷基）-锂试剂对映体特异性引入立体侧链，和（3）用于立体选择性引入螺旋轴的calphostins的高度阻转非对映体选择性Cu（I）促进的联芳基合成。总合成分别在13或14步中实现，具有极好的绝对立体化学控制。
The total syntheses of the perylenequinone natural products phleichrome and calphostin A are detailed. The syntheses were based on (1) the de novo construction of regiospecifically oxygenated and selectively protected naphthalene subunits, (2) the enantiospecific introduction of the stereogenic side chains using a chiral (alpha-alkoxyalkyl)-lithium reagent, and (3) a highly atropdiastereoselective Cu(I)-promoted biaryl synthesis for the stereoselective introduction of the helical axis of the calphostins. The total syntheses were achieved in 13 or 14 steps, respectively, with excellent control of absolute stereochemistry.