Total Synthesis of Highly Oxygenated Bisabolane Sesquiterpene Isolated from Ligularia lankongensis : Relative and Absolute Configurations of the Natural Product

作者：Kenichi Kobayashi, Risako Kunimura, Hirokazu Takagi, Misaki Hirai, Hiroshi Kogen, Hiroshi Hirota, Chiaki Kuroda · 发表于：The Journal of Organic Chemistry · 年份：2017 · DOI：10.1021/acs.joc.7b02688 · 被引用次数：12 · 研究领域：Plant Toxicity and Pharmacological Properties、Sesquiterpenes and Asteraceae Studies、Natural product bioactivities and synthesis

The relative and absolute configurations of an oxygenated bisabolane natural product, isolated from Ligularia lankongensis, were determined by synthesis. All four possible stereoisomers and their tiglate analogues were synthesized from R -(−)-carvone, and their 1 H and 13 C NMR spectra were compared to establish the 6 R,8 S,10 S configuration. The stereoselective synthesis of the natural product was also achieved, featuring Brown allylation, vanadium-catalyzed epoxidation, and the Mitsunobu reaction.