Synthesis of orthogonally protected azalanthionines (lanazanines) by sequential ring-opening of N-substituted aziridine 2-carboxylates
Orthogonally protected azalanthionines (lanazanines, 4-azadiaminopimelic acids or β-aminoalaninoalanines) have been synthesised in good yields by the ring-opening of N-protected aziridine 2-carboxylates with suitably protected diaminopropanoic acids (DAPs
Studies on the synthesis of orthogonally protected azalanthionines, and of routes towards β-methyl azalanthionines, by ring opening of N-activated aziridine-2-carboxylates
Orthogonally protected azalanthionines were successfully synthesised by the ring-opening of N-activated aziridine-2-carboxylates with protected diaminopropanoic acids (DAPs). The required DAPs were also prepared by ring-opening of N-activated aziridine-2-carboxylates with para-methoxybenzylamine, but it was found that the choice of aziridine protecting groups dictated both the success of the reaction as well as the regioselectivity of the isolated products. Attempts to extend the methodology to the preparation of the more sterically demanding β-methyl azalanthionines have, so far, been unsuccessful.
Studies on the synthesis of orthogonally protected azalanthionines, and of routes towards β-methyl azalanthionines, by ring opening of N-activated aziridine-2-carboxylates
Orthogonally protected azalanthionines were successfully synthesised by the ring-opening of N-activated aziridine-2-carboxylates with protected diaminopropanoic acids (DAPs). The required DAPs were also prepared by ring-opening of N-activated aziridine-2-carboxylates with para- methoxybenzylamine, but it was found that the choice of aziridine protecting groups dictated both the success of the reaction as well as the regioselectivity of the isolated products. Attempts to extend the methodology to the preparation of the more sterically demanding β-methyl azalanthionines have, so far, been unsuccessful.
Microwave-assisted ring-opening of activated aziridines with resin-bound amines
(Chemical Equation Presented) This paper describes the first study of nucleophilic ring-opening of nosylamide-activated aziridines under microwave irradiation conditions in solid-phase synthesis (SPS). The effects of solvent, temperature, reaction time, a
Crestey, Francois,Witt, Matthias,Frydenvang, Karla,Staerk, Dan,Jaroszewski, Jerzy W.,Franzyk, Henrik
p. 3566 - 3569
(2008/09/20)
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