异黄烷-3,4-二醇类化合物的合成研究

The synthesis of 3,4-dyhydroxy-isoflavanol compounds

目的以异黄烷酮为原料,探索顺式及反式异黄烷-3,4-二醇类化合物的合成路线。方法从商业易得的大豆素出发,通过还原α,β不饱和酮、苄位脱水等反应得到异黄烷-3-烯化合物后,再分别以顺式双羟化及环氧化-开环氧的策略探索顺式及反式邻二醇的合成。结果以四氧化锇作用下的双羟化反应,顺利实现了顺式异黄烷二醇的制备。对反式邻二醇的制备,尝试了环氧化再开环氧的策略,意外地得到了顺式邻二醇,而非期望的反式邻二醇。结论通过2条合成路线的探索,实现了异黄烷-3,4-二醇类化合物合成,为今后该类化合物的获得提供了新的途径。

Purposes—To synthesize syn-and anti-isoflav-3,4-diol compounds with isoflavanone as the raw material.Methods—The targeted products were prepared by syn-dihydroxylation and anti-dihydroxylation of isoflav-3-ene compounds,which were synthesized from daidzein via the reduction ofα,β-unsaturated ketone and dehydration reaction of benzyl alcohol.Result—The syn-3,4-diol was successfully synthesized by the oxidation of isoflav-3-ene with osmium tetroxide.The synthesis of anti-3,4-diol was studied via epoxidation and ring opening of epoxy,unexpectedly getting syn-3,4-diol,not the desired anti-3,4-diol.Conclusion—After the exploration of two synthetic routes,the synthesis of 3,4-dyhydroxy-isoflavanol is realized which provides a new way for produce these compounds.