Mao Zhuo-Ya, Si Chang-Mei, Liu Yi-Wen, Dong Han-Qing, Wei Bang-Guo, Lin Guo-Qiang
Department of Natural Products Chemistry, School of Pharmacy, Fudan University , 826 Zhangheng Road, Shanghai 201203, China.
Institutes of Biomedical Sciences, Fudan University , 130 Dongan Road, Shanghai 200032, China.
J Org Chem. 2016 Oct 21;81(20):9903-9911. doi: 10.1021/acs.joc.6b02086. Epub 2016 Oct 5.
An efficient method for asymmetric synthesis of apratoxin E 2 is described in this report. The chiral lactone 8, recycled from the degradation of saponin glycosides, was utilized to prepare the non-peptide fragment 6. In addition to this "from nature to nature" strategy, olefin cross-metathesis (CM) was applied as an alternative approach for the formation of the double bond. Moreover, pentafluorophenyl diphenylphosphinate was found to be an efficient condensation reagent for the macrocyclization.
本报告描述了一种高效不对称合成阿普拉毒素E 2的方法。从皂苷糖苷降解中回收的手性内酯8用于制备非肽片段6。除了这种“从天然到天然”的策略外，烯烃交叉复分解反应（CM）被用作形成双键的替代方法。此外，发现五氟苯基二苯基次膦酸酯是一种用于大环化的高效缩合试剂。
