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2024-01-30T10:19:55Z urn:hdl:10324/65281 Mimicking Halimane Synthases: Monitoring a Cascade of Cyclizations and Rearrangements from Epoxypolyprenes Quilez del Moral, José F. Domingo, Victoriano Pérez, Álvaro Martínez Andrade, Kevin A. López-Pérez, José Luis Barrero, Alejandro F. Enríquez Giraudo, María Lourdes Jaraíz Maldonado, Martín Producción Científica 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. 2024-01-30T10:19:55Z 2024-01-30T10:19:55Z 2019 info:eu-repo/semantics/article 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 eng https://doi.org/10.1021/acs.joc.9b01996 info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by-nc-nd/4.0/ Copyright © 2019 American Chemical Society Attribution-NonCommercial-NoDerivatives 4.0 Internacional American Chemical Society