222987-65-7Relevant academic research and scientific papers
First total synthesis of the 7,6′-coupled antifungal naphthylisoquinoline alkaloid dioncophylline
Bringmann, Gerhard,Günther, Christian,Peters, Eva-Maria,Peters, Karl
, p. 1253 - 1259 (2001)
The first total synthesis of the antimalarial alkaloid dioncophylline B (2) from Triphyophyllum peltatum (Dioncophyllaceae), and thus the first preparation of a 7,6′-coupled naphthylisoquinoline, is described. Key steps within this synthesis are the ortho-functionalization of the MOM-protected naphthalene and isoquinoline moieties 14 and 7 by directed ortho-metalation, with subsequent stannylation of the naphthalene part and bromination of the isoquinoline portion, and the regioselective intermolecular Stille coupling reaction of these building blocks. The presented synthesis opens the way for the preparation of further 7-coupled compounds of this class of alkaloids.
First total synthesis of dioncophylline b, a 7,6'-coupled naphthylisoquinoline alkaloid 1
Bringmann, Gerhard,Günther, Christian
, p. 216 - 218 (2007/10/03)
The total synthesis of dioncophylline B (2), a naphthylisoquinoline alkaloid with the rare 7,6′-coupling type and high antimalarial and fungicidal activities, is described. The key step of this convergent synthesis is the regioselective intermolecularbiaryl coupling of its appropriately modified naphthalene and isoquinoline moieties, with MOM-functionalized oxygen substituents next to the coupling sites: The naphthalene moiety is activated by a directed o/7/io-metalation -> stannylation procedure, while the isoquinoline part is metalated and then brominated ortho to the MOM-protected oxygen function, thus allowing a Stille coupling to connect the two parts. The work constitutes the first synthesis of any 7,6′-coupled naphthylisoquinoline alkaloid. Thieme Stuttgart.
