Yang Zhen-Ning, Rao Huijuanzi, Yin Yuhao, Mu Shan, Jia Ziqi, Ding Hanfeng
Department of Chemistry, Zhejiang University, Hangzhou 310058, China.
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China.
Org Lett. 2024 May 3;26(17):3524-3529. doi: 10.1021/acs.orglett.4c00885. Epub 2024 Apr 24.
A ring distortion approach for the synthesis of an advanced intermediate en route to rhodomolleins XIV and XLII was described, which led to successful construction of the 5/8/5/5 tetracyclic core framework of the kalmane diterpenoids. Key steps of the strategy include an oxidative dearomatization-induced (ODI)-Diels-Alder cycloaddition, a Dowd-Beckwith rearrangement, and a bioinspired Wagner-Meerwein rearrangement.
描述了一种用于合成通往红景天素XIV和XLII途中的高级中间体的环扭曲方法，该方法成功构建了kalmane二萜类化合物的5/8/5/5四环核心骨架。该策略的关键步骤包括氧化脱芳构化诱导（ODI）-狄尔斯-阿尔德环加成反应、多德-贝克威思重排反应和仿生瓦格纳-米尔温重排反应。
