Organic Chemistry Division-I, Indian Institute of Chemical Technology (CSIR), Hyderabad 500007, India.
J Org Chem. 2009 Nov 20;74(22):8822-5. doi: 10.1021/jo901913h.
A highly stereoselective formal total synthesis of the ornithine decarboxylase inhibitors (-)-saliniketals A and B is described. The salient features of the synthesis are the utilization of a desymmetrization technique to create six contiguous chiral centers from a single bicyclic precursor as well as substrate-controlled Grignard reaction, intramolecular Wacker-type oxidation, and antialdol reaction following Pirrung-Heathcock conditions.
本文描述了一种高度对映选择性的正式全合成方法,用于合成鸟氨酸脱羧酶抑制剂(-)-沙林酮 A 和 B。该合成的显著特点是利用去对称化技术,从单个双环前体中构建六个连续的手性中心,以及受底物控制的格氏反应、分子内 Wacker 型氧化和 Pirrung-Heathcock 条件下的反羟醛缩合反应。