2,3-Secooleanane hydroxynitriles undergo dehydration and anionotropic 1,2-migration of the methyl group C(24)H3 under the action of the SOCl2-CH2Cl2 system to form a mixture of isomeric Δ4-alkenes. A similar E1-elimination process in the presence of the H2SO4—AcOH system is accompanied by hydrolysis of the CN group giving A-ring unsaturated C(2)-ketones and diastereomeric ε-lactones. Epimeric 4,23-epoxides and isopropyl ketone were synthesized by oxidative transformations of 4,23-alkene, which was selectively formed from 2,3-secooleanane hydroxynitrile under the action of the POCl3-Py system. The in vitro cytotoxic evaluation by the MTT assay showed that the synthesized compounds are not toxic (IC50 > 100 μmol L−1) against the human cancer cell lines HEp-2, HCT116, MS, RD TE32, MCF-7, A549, and PC-3.

中文翻译：

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A-seco-18αH-齐墩果烷羟基腈的转化

2,3-癸烷羟基腈在SOCl2-CH2Cl2体系的作用下，甲基C(24)H3发生脱水和阴离子性1,2-迁移，形成异构Δ4-烯烃的混合物。在 H2SO4-AcOH 系统存在下，类似的 E1 消除过程伴随着 CN 基团的水解，产生 A 环不饱和 C(2)-酮和非对映异构体 ε-内酯。差向异构 4,23-环氧化物和异丙基酮是通过 4,23-烯烃的氧化转化合成的，4,23-烯烃是在 POCl3-Py 系统的作用下由 2,3-secooleanane 羟基腈选择性形成的。MTT 法体外细胞毒性评估表明，合成的化合物对人癌细胞系 HEp-2、HCT116、MS、RD TE32、MCF-7、A549 和个人电脑-3。