Tello-Aburto Rodolfo, Olivo Horacio F
Division of Medicine and Natural Products Chemistry, The University of Iowa, Iowa City, Iowa 52242, USA.
Org Lett. 2008 Jun 5;10(11):2191-4. doi: 10.1021/ol8005908. Epub 2008 May 8.
A highly convergent formal synthesis of the auriside aglycon was achieved. An indene-based thiazolidinethione chiral auxiliary was used for the construction of both the C1-C9 and C10-C17 fragments via acetate aldol reactions. A Meinwald reaction was utilized to install the stereocenter at C2, and a conjugated addition to an ynone was used to construct the C9-C11 enone.
实现了奥瑞西甙元的高度汇聚式形式合成。一种基于茚的噻唑烷硫酮手性助剂通过乙酸酯羟醛反应用于构建C1-C9和C10-C17片段。利用迈因瓦尔德反应在C2处安装立体中心,并利用向炔酮的共轭加成构建C9-C11烯酮。