Freeman-Cook K D, Halcomb R L
Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, USA.
J Org Chem. 2000 Sep 22;65(19):6153-9. doi: 10.1021/jo000665j.
A symmetry-based strategy for the synthesis of the zaragozic acids is reported. Two enantioselective dihydroxylations were used to establish the absolute configuration of a C(2) symmetric intermediate. Noteworthy transformations include a group-selective lactonization, which accomplished an end-differentiation of a pseudo-C(2) symmetric intermediate. Late stage protecting group adjustments and oxidations accomplished a formal synthesis of zaragozic acid A.
报道了一种基于对称性的扎拉戈昔酸合成策略。使用了两次对映选择性二羟基化反应来确定一个C(2)对称中间体的绝对构型。值得注意的转化包括一个基团选择性内酯化反应，该反应实现了一个假C(2)对称中间体的末端区分。后期的保护基调整和氧化反应完成了扎拉戈昔酸A的形式合成。
