PhD conferral Jordy M. Saya



Aula, Vrije Universiteit Amsterdam

Tryptamine-Derived Isocyanides I Have Known and Loved

Jordy M. Saya

Prof.Dr. Ir. R.V.A. Orru, copromotor Dr. E. Ruijter


Amsterdam Institute for Molecules, Medicines and Systems


PhD conferral

Tryptamine-Derived Isocyanides I Have Known and Loved:
From Multicomponent Reactions to Natural Product Synthesis

Driven by natural selection, Nature has composed a preferred collection of molecular fragments that have shaped its rich repertoire of chemical structures. Tryptamine can be considered as such a so-called privileged structure, as it is incorporated in a great variety of natural occurring alkaloids. Especially monoterpenoid indole alkaloids are highly abundant and have attracted great interest from the organic chemistry community. Although nowadays many monoterpenoid indole alkaloids have been synthesized, alternative synthetic strategies continuously appear in the literature, mainly with the aim to showcase new synthetic methodologies. This research was based on our interest to exploit the reactivity of tryptamine-derived isocyanides in alternative synthetic approaches towards Aspidospermaand Strychnos type indole alkaloids. Driven by this curiosity, we successfully realized the formal total synthesis of aspidofractinine. Furthermore, our studies revealed several new insights in both indole and isocyanide chemistry.

Jordy M. Saya