Divergent Total Syntheses to Azafluoranthene and Dehydroaporphine Alkaloids

作者：Khunnawutmanotham Nisachon; Sahakitpichan Poolsak; Chimnoi Nitirat; Techasakul Supanna^*

来源：European Journal of Organic Chemistry, 2015, 2015(28): 6324-6332.

DOI：10.1002/ejoc.201500866

• Alkaloids
• Synthetic methods
• Natural products
• Divergent synthesis
• Polycycles
• Domino reactions

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.

• 出版日期2015-10