915304-99-3Relevant academic research and scientific papers
Synthesis of (±)-aureol by bioinspired rearrangements
Rosales, Antonio,Mu?oz-Bascón, Juan,Roldan-Molina, Esther,Rivas-Bascón, Nazaret,Padial, Natalia M.,Rodríguez-Maecker, Roman,Rodríguez-García, Ignacio,Oltra, J. Enrique
, p. 1866 - 1870 (2015)
A bioinspired and sustainable procedure for the straightforward synthesis of (±)-aureol has been achieved in eight steps (14% overall yield) from epoxyfarnesol. The key steps are the titanocene(III)-catalyzed radical cascade cyclization of an epoxyfarneso
Transition-metal-catalyzed allylic substitution and titanocene-catalyzed epoxypolyene cyclization as a powerful tool for the preparation of terpenoids
Gansaeuer, Andreas,Justicia, Jose,Rosales, Antonio,Worgull, Dennis,Rinker, Bjoern,Cuerva, Juan Manuel,Oltra, Juan Enrique
, p. 4115 - 4127 (2007/10/03)
Many biologically active substances are composed of sesquiterpene units linked to aromatic structures, especially substituted phenols. Here, we describe an efficient synthetic approach to this class of natural product from commercially available substances in a short sequence. The key transformations involve allylic substitution reactions using a palladium or copper catalyst and titanocene-catalyzed epoxypolyene cyclization reactions via radicals. The polycyclic core structures are accessed with high chemo- and stereocontrol. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
