1227009-31-5Relevant articles and documents
Two versatile and parallel approaches to highly symmetrical open and closed natural product-based structures
Montenegro, Hector E.,Ramirez-Lopez, Pedro,De La Torre, Maria C.,Asenjo, Maria,Sierra, Miguel A.
supporting information; experimental part, p. 3798 - 3814 (2010/07/05)
Two parallel approaches for preparing diverse and highly symmetrical homohybrids derived from a series of mono- and diterpenes, steroids, and alkaloids are reported. Both procedures are based on the mono-addition of bis(alkynyl) dilithium reagents to natural products having a carbonyl group to produce the corresponding al-kynyl derivatives. The Glaser-Hay Cu-promoted homocoupling of these al-kynyl natural product mono-adducts as well as the Huisgen Cu-catalyzed azide-alkyne cycloaddition (CuAAC) reaction resulted in the synthesis of ste-roid-, terpene-, and alkaloid-based ho-mohybrid derivatives incorporating di-verse spacers to join the natural product scaffolds. Straightforward entries to novel closed highly symmetrical and complex estrone-based macrocyclic and cage architectures by means of the Glaser-Eglinton homocoupling and the CuAAC reaction have been devised.