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00925njm 22002777a 4500 dc Quilez del Moral, José F. author Domingo, Victoriano author Pérez, Álvaro author Martínez Andrade, Kevin A. author López-Pérez, José Luis author Barrero, Alejandro F. author Enríquez Giraudo, María Lourdes author Jaraíz Maldonado, Martín author 2019 We have developed and rationalized a biomimetic transformation mimicking halimane synthases based on a Lewis acid-catalyzed cascade of cyclizations and rearrangements of epoxypolyprenes. Two rings, three stereogenic centers, and a new double bond were generated in a single chemical operation. Based on this cascade transformation, we achieved a unified strategy toward the stereoselective total syntheses of halimene-type terpenoids and analogues as a proof-of-concept study. This method has been applied to the rapid synthesis of diterpene isotuberculosinol, a virulence factor of Mycobacterium tuberculosis as a representative example. J. Org. Chem. 2019, 84, 21, 13764–13779 0022-3263 https://uvadoc.uva.es/handle/10324/65281 10.1021/acs.joc.9b01996 13764 21 13779 The Journal of Organic Chemistry 84 1520-6904 Mimicking Halimane Synthases: Monitoring a Cascade of Cyclizations and Rearrangements from Epoxypolyprenes