Annulation of isoquinoline and β-carboline using olefinic metathesis

Abstract

Isoquinoline and β-carboline derivatives are a large class of naturally occurring compounds. These compounds show variety of biological properties and as such they have been a subject of intensive research. Structural variations attracted attention from organic chemists as well and a number of synthesis for the preparation of these systems have been reported in the literature. Our strategy was based on annelation of the isoquinoline and β-carboline skeleton via ring closing metathesis reaction and further functionalization of the obtained product to more complex structures.

Izohinolinski i β-karbolinski skelet je prisutan u velikom broju prirodnih proizvoda, koji pokazuju širok spektar bioloških aktivnosti. Raznolikost njihovih struktura već godinama privlači pažnju organskih hemičara, pa su razvijene i brojne metode za sintezu ovih jedinjenja. U cilju razvoja alternativnog sintetskog pristupa, u našim laboratorijama proučavani su procesi anelacije izohinolinskog i β-karbolinskog skeleta zasnovani na reakciji olefinske metateze. Na ovaj način dobijene su strukture koje potencijalno mogu biti upotrebljene u sintezi kompleksnijih molekula, uključujući i neke klase prirodnih proizvoda zasnovanih na pomenutim heterocikličnim jedinjenjima.