Institutes of Biomedical Sciences and School of Pharmacy, Fudan University , 220 Handan Road, Shanghai 200433, China.
Xinjiang Institute of Materia Medica , Lane 140, South Xinhua Road, Urumqi, Xinjiang 830004, China.
Org Lett. 2017 Dec 15;19(24):6732-6735. doi: 10.1021/acs.orglett.7b03459. Epub 2017 Dec 6.
In this report, the originally proposed rupestonic acid (5) and pechueloic acid (3) were efficiently synthesized. The chiral lactone 13, recycled from the degradation of saponin glycosides, was utilized to prepare the key chiral fragment 11. During the exploration of this convergent assembly strategy, the ring-closing metathesis (RCM), SmI-prompted intermolecular addition, and [2,3]-Wittig rearrangement proved to be effective transformations for the synthesis of subunits.
在本报告中，高效合成了原本提出的岩蔷薇酸（5）和柏醇酸（3）。利用从皂苷糖苷降解中回收的手性内酯 13 来制备关键的手性片段 11。在探索这种收敛组装策略的过程中，闭环复分解（RCM）、SmI 引发的分子间加成和[2,3]-Wittig 重排被证明是合成亚基的有效转化。
