A Maze of Dyotropic Rearrangements and Triple Shifts: Carbocation Rearrangements Connecting Stemarene, Stemodene, Betaerdene, Aphidicolene, and Scopadulanol

The Journal of Organic Chemistry
Young J Hong, Dean J Tantillo

Abstract

Results of quantum chemical investigations shed new light on the mechanisms of formation of the stemarene, stemodene, betaerdene, aphidicolene, and scopadulanol diterpenes from syn-copalyl diphosphate ( syn-CPP). These terpenes are shown to be connected by a complex network of reaction pathways involving concerted but asynchronous dyotropic rearrangements and triple shift rearrangements. The interconnection of these pathways leads to multiple routes for formation of each diterpene, which could lead to different origins for some carbon atoms in a given diterpenes under different conditions.

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Citations

May 31, 2019·International Journal of Molecular Sciences·Francesca LeonelliRinaldo Marini Bettolo
May 8, 2020·Chemical & Pharmaceutical Bulletin·Hajime SatoMasanobu Uchiyama
Dec 20, 2019·Journal of the American Chemical Society·Vladislav A RoytmanDaniel A Singleton
Jan 10, 2019·Journal of the American Chemical Society·Xiao-Song XueK N Houk
Jan 6, 2021·Journal of the American Chemical Society·Zhitao Feng, Dean J Tantillo

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