N. Zefirov, Yana S. Glazkova, I. Kuznetsova
Jun 3, 2015
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Journal
Moscow University Chemistry Bulletin
Abstract
Based on molecular modeling data, 2-adamantyl 8-[(2-methoxyestra-1,3,5(10)-triene-3,17β-diol-6α-yl)amino]octanoate 2d is proposed as a structural analogue of highly cytotoxic N-(8-(adamant-2-yloxi)-8-oxooctanoyl)-N-deacetylcolchycine. Three-step synthesis of adamant-2-yl 8-aminooctanoate 5 is described. Reductive amination of 2-methoxy-6-oxo-17β-estradiol in weakly acidic medium in the presence of compound 5 and NaBH3CN or Na(OAc)3BH results in the product of elimination at the C6–C7 bond of steroid 7 rather than the formation of conjugate 2d.