Synthesis of new camptothecin analogues with the E-lactone ring replaced by α,β-cyclohexenone

Valeriy A. Bacherikov, Tsong Jen Tsai, Jang Yang Chang, Ting Chao Chou, Rong Zau Lee, Tsann Long Su

研究成果: Article同行評審

7 引文 斯高帕斯(Scopus)

摘要

The total synthesis of racemic camptothecin analogues 12a and 12b, in which the E-lactone ring has been replaced by an α,β-cyclohexenone ring and the ethyl and hydroxy substituents have been retained, was achieved by first preparing the ABCD fragments 31a and 31b, which were then converted into the tetracyclic triol 36a and 36b by osmium-mediated dihydroxylation. Compounds 36a and 36b were oxidized in one-pot reactions, followed by intramolecular aldol condensation to furnish the desired pentacyclic 12a and 12b, which retained topoisomerase I inhibitory activity and exhibited cytotoxicity to tumor cell growth in culture.

原文English
頁(從 - 到)4490-4499
頁數10
期刊European Journal of Organic Chemistry
發行號19
DOIs
出版狀態Published - 2006 九月 25

All Science Journal Classification (ASJC) codes

  • 物理與理論化學
  • 有機化學

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