78416-88-3Relevant articles and documents
Divergent Total Syntheses to Azafluoranthene and Dehydroaporphine Alkaloids
Khunnawutmanotham, Nisachon,Sahakitpichan, Poolsak,Chimnoi, Nitirat,Techasakul, Supanna
, p. 6324 - 6332 (2015)
Facile divergent total syntheses for azafluoranthene and dehydroaporphine alkaloids have been successfully developed. A common intermediate, a biarylsulfonamide-protected amino aldehyde, underwent either a cascade or a stepwise cyclization to furnish a tetracyclic skeleton related to the azafluoranthene alkaloids. Natural products, triclisine and telitoxine, were prepared to illustrate the use of this approach. Subsequent C-homologation of the aldehyde moiety on the same intermediate by means of a Wittig reaction allowed the synthesis of aporphine alkaloids, as exemplified by the preparation of dehydronornuciferine. This synthetic approach could be applicable to the syntheses of other azafluoranthene-related as well as aporphine-related alkaloids. Facile divergent syntheses for azafluoranthene and dehydroaporphine alkaloids are reported by using a biarylsulfonamide-protected amino aldehyde as a common intermediate. The natural azafluoranthenes, triclisine and telitoxine, and an aporphine alkaloid, dehydronornuciferine, were prepared to illustrate the use of this approach.