72311-08-1Relevant academic research and scientific papers
Highly Stereocontrolled Total Syntheses of Cedrane Sesquiterpenes via Cascade [5+2] Cycloaddition/Etherification
Chi, Zhiyong,Li, Xiangxin,Xie, Zhixiang,Zhang, Yuhan
supporting information, p. 183 - 189 (2021/12/21)
Cedrane sesquiterpenes possess common tricyclo[5.3.1.01,5]undecane core structure. The varied oxa-five-membered ring decorating their core structure to form 8-oxa-tetracyclo[7.2.2.01,5.06,13]tridecane framework, containing six consecutive chiral centers (including two all-carbon quaternary centers and one oxygenated quaternary carbon center), has proven to be a synthetic challenge and a biosynthetic mystery to date. Herein, we reported a distinct and biomimetic strategy to these sesquiterpenes resulting in the concise asymmetric total syntheses of three cedrane sesquiterpenes from simple commercially available building blocks. Key feature is exploitation of a cascade oxidative dearomatization-induced [5+2] cycloaddition/etherification to highly stereocontrolled construct 8-oxa-tetracyclo[7.2.2.01,5.06,13]tridecane framework with five contiguous chiral centers in one step. In addition, a metal-free I2-catalyzed and DMSO-mediated oxidative dehydroaromatization was applied to prepare curcuphenol and its derivatives from the highly functionalized cyclohexenones with minimal manipulations.
Total synthesis of bisabolane sesquiterpenoids, α-bisabol-1-one, curcumene, curcuphenol and elvirol: Utility of catalytic enamine reaction in cyclohexenone synthesis
Hagiwara, Hisahiro,Okabe, Tomoyuki,Ono, Hiroki,Kamat, Vijayendra P.,Hoshi, Takashi,Suzuki, Toshio,Ando, Masayoshi
, p. 895 - 900 (2007/10/03)
Total syntheses of α-bisabol-1-one, curcumene, curcuphenol and elvirol have been accomplished via 1,4-conjugate addition of intact aldehydes to vinyl ketones followed by an intramolecular aldol condensation.
