Department of Chemistry, The Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA.
J Org Chem. 2011 Jun 17;76(12):5149-55. doi: 10.1021/jo200795f. Epub 2011 May 20.
New chlorodiols (±)-3 and (±)-5 are densely functionalized and versatile synthons. They are converted in one step on a gram scale into 2-chlorolactones (±)-6 and (±)-7 and into 4-hydroxy glycidate esters (±)-9 and (±)-10. The 4-hydroxy glycidate esters (±)-9 and (±)-10 are converted stereospecifically and regiospecifically into oxazolines (±)-13 and (±)-14 and into cyclic carbamates (±)-18-(±)-20. The 4-hydroxy glycidate ester (±)-10 undergoes stereocontrolled and regiocontrolled epoxide opening by sodium azide to form the 2-azido-3,4-dihydroxy alkanoate (±)-21. Finally, chlorodiol (±)-5 reacts stereospecifically with silver triflate to form the 2,3-dihydroxyfuranone (±)-26.
新型氯代二醇（±）-3 和（±）-5 具有高度功能化和多功能的合成子。它们可以在克级规模上一步转化为 2-氯内酯（±）-6 和（±）-7，以及 4-羟基缩水甘油酸酯（±）-9 和（±）-10。4-羟基缩水甘油酸酯（±）-9 和（±）-10 可以立体选择性和区域选择性地转化为恶唑啉（±）-13 和（±）-14 以及环状碳酸酯（±）-18-（±）-20。4-羟基缩水甘油酸酯（±）-10 可以通过叠氮化钠进行立体控制和区域控制的环氧化物开环反应，形成 2-叠氮基-3,4-二羟基烷酸酯（±）-21。最后，氯代二醇（±）-5 与三氟甲磺酸银反应，立体专一性地形成 2,3-二羟基呋喃酮（±）-26。
