RT info:eu-repo/semantics/article
T1 Mimicking Halimane Synthases: Monitoring a Cascade of Cyclizations and Rearrangements from Epoxypolyprenes
A1 Quilez del Moral, José F.
A1 Domingo, Victoriano
A1 Pérez, Álvaro
A1 Martínez Andrade, Kevin A.
A1 López-Pérez, José Luis
A1 Barrero, Alejandro F.
A1 Enríquez Giraudo, María Lourdes
A1 Jaraíz Maldonado, Martín
AB 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.
PB American Chemical Society
SN 0022-3263
YR 2019
FD 2019
LK https://uvadoc.uva.es/handle/10324/65281
UL https://uvadoc.uva.es/handle/10324/65281
LA eng
NO J. Org. Chem. 2019, 84, 21, 13764–13779
NO Producción Científica
DS UVaDOC
RD 18-nov-2024