A novel total synthesis of isocryptolepine based on a microwave-assisted tandem Curtius rearrangement and aza-electrocyclic reaction
A new entry to the total synthesis of isocryptolepine (cryptosanguinolentine), isolated from Cryptolepis sanguinolenta, was achieved by constructing a tetracyclic ring system through a microwave-assisted tandem Curtius rearrangement and electrocyclic reac
Synthesis of indolobenzazepinones by application of an isocyanide-based multicomponent reaction
Application of a Ugi multicomponent reaction to oxo acids 4 allows the formation of potentially antimitotic indolobenzazepinones of type 5 in good yields of up to 72%, whereas the same transformation from the starting substrate 6 gives access to analogues of paullone with yields of up to 89%. The reaction could be applied to a wide range of isocyanides, thereby ensuring introduction of molecular diversity at the key C-5 position. Use of cyclohexenyl isocyanide allows post-condensation modifications, while careful choice of the amine and the indole protecting groups proved to be important for providing the deprotected compounds necessary for biological tests. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Beaumont, Stephane,Retailleau, Pascal,Dauban, Philippe,Dodd, Robert H.
experimental part
p. 5162 - 5175
(2009/05/07)
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