Whitehead Alan, Waetzig Joshua D, Thomas Christopher D, Hanson Paul R
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA.
Org Lett. 2008 Apr 3;10(7):1421-4. doi: 10.1021/ol8001865. Epub 2008 Mar 7.
Construction of the C15-C30 subunit of dolabelide utilizing a temporary phosphate tether is described. Two routes are reported that make use of the orthogonal protecting- and leaving-group properties innate to phosphate esters. One route relies on a selective terminal oxidation, while a second utilizes a CM/selective hydrogenation sequence. Both routes depend on a highly regio- and diastereoselective cuprate addition to set the requisite stereochemistry at C22.
描述了利用临时磷酸酯连接基构建多拉贝利德C15 - C30亚基的方法。报道了两条利用磷酸酯固有的正交保护基和离去基团性质的路线。一条路线依赖于选择性末端氧化，而另一条路线利用CM/选择性氢化序列。两条路线都依赖于高度区域和非对映选择性的铜酸盐加成，以在C22处设定所需的立体化学。
