Bose Gopal, Bracht Karin, Bednarski Patrick J, Lalk Michael, Langer Peter
Institut für Chemie und Biochemie, Universität Greifswald, Soldmannstr. 16, 17487 Greifswald, Germany.
Bioorg Med Chem. 2006 Jul 15;14(14):4694-703. doi: 10.1016/j.bmc.2006.03.037. Epub 2006 Apr 17.
1-Hydroxyspiro[2.5]cyclooct-4-en-3-ones-analogs of natural illudines--were prepared in good yields by cyclization of 1,3-dicarbonyl dianions or 1,3-bis-silyl enol ethers ('masked dianions') with 1,1-diacylcyclopropanes. Several spirocyclopropanes showed a significant antiproliferative activity against human leukemia HL60 cells in vitro. 1-Hydroxyspiro[2.5]cyclooct-4-en-3-ones represent highly reactive precursors of unstable spiro[5.2]cycloocta-4,7-dien-6-ones and reactions with a number of nucleophiles were studied.
1-羟基螺[2.5]环辛-4-烯-3-酮——天然伊鲁丁类似物——通过1,3-二羰基二阴离子或1,3-双硅烯醇醚（“掩蔽二阴离子”）与1,1-二酰基环丙烷环化反应以良好产率制备得到。几种螺环丙烷在体外对人白血病HL60细胞表现出显著的抗增殖活性。1-羟基螺[2.5]环辛-4-烯-3-酮是不稳定的螺[5.2]环辛-4,7-二烯-6-酮的高反应性前体，并对其与多种亲核试剂的反应进行了研究。
