König Christian M, Gebhardt Björn, Schleth Cornelia, Dauber Mario, Koert Ulrich
Fachbereich Chemie, Philipps-University Marburg, Hans-Meerwein-Strasse, D-35032 Marburg, Germany.
Org Lett. 2009 Jul 2;11(13):2728-31. doi: 10.1021/ol900757k.
A convergent total synthesis of the PP2A-inhibitor phoslactomycin A was achieved using a CuTC-mediated coupling of an alkenyl iodide C1-C13 fragment with an C14-C21 alkenyl stannane in the presence of a protected phosphate. Key features for the assembly of the C1-C13 fragment were an asymmetric dihydroxylation, an Evans-Aldol reaction, and a well-balanced protective group strategy. An asymmetric 1,4-addition to cyclohexenone was the key step in the preparation of the C14-C21 fragment.
通过在受保护的磷酸盐存在下，使用CuTC介导的碘代烯烃C1-C13片段与C14-C21烯基锡烷的偶联反应，实现了PP2A抑制剂磷雷霉素A的汇聚式全合成。C1-C13片段组装的关键特征包括不对称双羟基化、埃文斯-羟醛反应和平衡良好的保护基策略。对环己烯酮的不对称1,4-加成是制备C14-C21片段的关键步骤。
