Atatürk University, Faculty of Science, Department of Chemistry, TR-25240, Erzurum, Turkey.
Beilstein J Org Chem. 2010 Feb 15;6:15. doi: 10.3762/bjoc.6.15.
A new class of aminocyclitol derivatives with the bicyclo[4.2.0]octane skeleton was synthesized starting from cyclooctatetraene. Photooxygenation of trans-7,8-diacetoxy- and cis-7,8-dichlorobicyclo[4.2.0]octa-2,4-diene afforded the bicyclic endoperoxides. Reduction of the latter with thiourea followed by a Pd(0) catalyzed ionization/cyclization reaction gave the corresponding oxazolidinone derivatives. Oxidation of the double bond with KMnO₄ or OsO₄ followed by acetylation gave the acetate derivatives, the exact configuration of which was determined by spectroscopic methods. Hydrolysis of the oxazolidinone rings and removal of the acetate groups furnished the desired aminocyclitols.
从环辛四烯出发，合成了具有双环[4.2.0]辛烷骨架的新型氨基环糖醇衍生物。反式-7,8-二乙酰氧基-和顺式-7,8-二氯双环[4.2.0]辛-2,4-二烯的光氧化作用得到双环内过氧化物。后者用硫脲还原，然后用钯（0）催化的离子化/环化反应得到相应的恶唑烷酮衍生物。用 KMnO₄或 OsO₄氧化双键，然后进行乙酰化得到乙酸酯衍生物，其确切构型通过光谱方法确定。恶唑烷酮环的水解和乙酸酯基团的去除得到所需的氨基环糖醇。
