American Chemical Society
ja2c01692_si_001.pdf (5.34 MB)

Enantioselective Total Syntheses of Grayanane Diterpenoids: (−)-Grayanotoxin III, (+)-Principinol E, and (−)-Rhodomollein XX

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journal contribution
posted on 2022-03-17, 14:24 authored by Lingran Kong, Hang Yu, Mengping Deng, Fanrui Wu, Zhe Jiang, Tuoping Luo
Enantioselective total syntheses of (−)-grayanotoxin III, (+)-principinol E, and (−)-rhodomollein XX were accomplished based on a convergent strategy. The left- and right-wing fragments were assembled via the diastereoselective Mukaiyama aldol reaction catalyzed by a chiral hydrogen bond donor. The unique 7-endo-trig cyclization based on a bridgehead carbocation forged the 5/7/6/5 tetracyclic skeleton that underwent redox manipulations and 1,2-migration to access different grayanane diterpenoids.