Syntheses of naturally occurring cytotoxic [7.7]paracyclophanes, (-)-cylindrocyclophane A and its enantiomer, and implications for biological activity
Syntheses of naturally occurring cytotoxic [7.7]paracyclophanes, (-)-cylindrocyclophane A and its enantiomer, and implications for biological activity
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DOI：
10.1039/b909646a
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发表时间：
2009-01-01
影响因子：
3.2
通讯作者：
Iwabuchi, Yoshiharu
中科院分区：
文献类型：
--
作者：
Yamakoshi, Hiroyuki;Ikarashi, Fumiya;Iwabuchi, Yoshiharu
以手性炔丙醇为起始原料，采用Smith交叉复分解/闭环复分解反应为关键步骤，以对映体分散的方式，全合成了（-）-cylindrocyclophane A（1）及其对映体。对cylindrocyclophane A的两种对映体（1和ent-1）及其类似物的生物学评价表明，1的手性与其细胞毒性无关，这归因于嵌入在稳健的[7.7]对环蕃框架中的间苯二酚基序。
The total syntheses of (-)-cylindrocyclophane A (1), a naturally occurring, cytotoxic [7.7]paracyclophane, and its enantiomer have been achieved in an enantiodivergent manner starting from a chiral propargyl alcohol building block using Smith's cross metathesis/ring-closing metathesis protocol as the key step. The biological evaluation of both enantiomers of cylindrocyclophane A (1 and ent-1) and its analogues indicated that the chirality of 1 is irrelevant to its cytotoxicity, which is attributed to the resorcinol motifs embedded in the robust [7.7] paracyclophane framework.