Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, Tamil Nadu, India.
Org Lett. 2022 Jun 17;24(23):4240-4245. doi: 10.1021/acs.orglett.2c01531. Epub 2022 Jun 6.
A facile domino strategy has been developed for the synthesis of a biologically active cyclopent-2-enone core containing combretastatin A-4 (CA-4) analogues from aryloxirane and aryl aldehyde. This one-pot method involves a sequence of semipinacol rearrangement, iterative aldol condensation, and iso-Nazarov cyclization reactions. The scope of this methodology is further shown in the enantioselective synthesis of 5-hydroxy-cyclopent-2-enones using the Sharpless AD catalyst. Biological studies reveal that ()-enantiomers exhibit better inhibitory activity against cell proliferation than ()-enantiomers.
已开发出一种简便的多米诺策略，用于从芳基环氧乙烷和芳基醛合成含有康普瑞汀 A-4（CA-4）类似物的生物活性环戊-2-烯酮核心。该一锅法涉及半频哪醇重排、迭代羟醛缩合和异-Nazarov 环化反应的序列。该方法的范围还进一步显示在使用 Sharpless AD 催化剂的 5-羟基-环戊-2-烯酮的对映选择性合成中。生物研究表明，（）-对映异构体对细胞增殖的抑制活性优于（）-对映异构体。
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