title: Towards the Total Synthesis of Pl-3: Preparation of the Eastern Fragment through a Diastereoselective SmI2-Mediated Reformatsky Reaction.
abstract: The jatrophane diterpene Pl-3, isolated in 2003 fromEuphorbia platyphyllos, is a structurally complex natural product with highly promising biological properties that include pronounced antiproliferative activity and the inhibition of the efflux-pump activity of multidrug resistance p-glycoprotein. Herein, the synthesis of the eastern fragment of Pl-3 is outlined. The target compound is synthesized in nine synthetic operations in good overall yield, starting from readily available d-ribose. The key step in the preparation of the eastern part of Pl-3 is a diastereoselective SmI2-mediated Reformatsky reaction. The proposed route is highly flexible and could also be applied to the synthesis of structurally related jatrophane diterpenes.
authors.affiliation: Department of Organic Chemistry, University of Vienna Währinger Straße 38, 1090 Vienna, Austria , E-mail: uwe.rinner@univie.ac.at Homepage: http://rinner-group.univie.ac.at.
authors.forename: Rita
authors.initials: R
authors.lastname: Fürst
authors.forename: Christoph
authors.initials: C
authors.lastname: Lentsch
authors.forename: Uwe
authors.initials: U
authors.lastname: Rinner
keywords: Diastereoselectivity; Multi­drug resistance; Natural products; Samarium; Terpenoids