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Divergent Total Syntheses to Azafluoranthene and Dehydroaporphine Alkaloids
Author(s) -
Khunnawutmanotham Nisachon,
Sahakitpichan Poolsak,
Chimnoi Nitirat,
Techasakul Supanna
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500866
Subject(s) - chemistry , aldehyde , moiety , total synthesis , wittig reaction , aporphine , stereochemistry , alkaloid , organic chemistry , catalysis
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.