866474-71-7Relevant academic research and scientific papers
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 (2006)
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.
Indium tribromide-promoted arene-terminated epoxy olefin cyclization
Zhao, Jun-Feng,Zhao, Yu-Jun,Loh, Teck-Peng
, p. 1353 - 1355 (2008/12/21)
An arene-terminated epoxy olefin cyclization was promoted by a water-tolerant Lewis acid to give tri- and tetracyclic 3β-hydroxy terpenoids and steroid derivatives in 57 and 37% yields, respectively, per new formed ring up to 75%. The Royal Society of Chemistry.
Efficient and stereoselective synthesis of precursors for epoxypolyene cyclizations via allylic substitutions
Gans?uer, Andreas,Justicia, José,Rosales, Antonio,Rinker, Bj?rn
, p. 1954 - 1956 (2007/10/03)
A catalytic and highly stereoselective approach to precursors for epoxypolyene cyclizations based on copper-catalyzed allylic substitutions is described. The method allows introduction of various aromatic, benzyl, and alkyl groups without affecting epoxides. The compounds obtained are valuable starting materials for the synthesis of natural products and biologically active substances. Georg Thieme Verlag Stuttgart.
