Baran Arif, Günel Aslihan, Balci Metin
Department of Chemistry, Middle East Technical University, Ankara, Turkey.
J Org Chem. 2008 Jun 20;73(12):4370-5. doi: 10.1021/jo800553u. Epub 2008 May 20.
For the construction of the bicyclo[2.2.2]octane skeleton, 2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole was reacted with vinylene carbonate to give two isomeric cycloadditon products having the bicyclo[2.2.2]octane skeleton. Hydrolysis of the ketal ring and the opening of the carbonate functionality, followed by hydroxylation of the remaining double bond resulted in the formation of a symmetrical hexol. Epoxidation of the double bond in the cycloaddition products and the subsequent ring-opening reactions produce two additional hexol derivatives. One of the synthesized molecules exhibited enzyme-specific inhibition against alpha-glycosidase.
为构建双环[2.2.2]辛烷骨架，使2,2 - 二甲基 - 3a,7a - 二氢 - 1,3 - 苯并二恶唑与碳酸亚乙烯酯反应，得到两种具有双环[2.2.2]辛烷骨架的异构环加成产物。缩酮环的水解和碳酸酯官能团的开环，随后对剩余双键进行羟基化，导致形成一种对称的己糖醇。环加成产物中双键的环氧化以及随后的开环反应产生了另外两种己糖醇衍生物。所合成的分子之一表现出对α - 糖苷酶的酶特异性抑制作用。
