Novel spirocyclic systems via multicomponent aza-Diels–Alder reaction

Sabin Llona-Minguez; Adam Throup; Emilie Steiner; Molly Lightowler; Sandra Van der Haegen; Evert Homan; Lars Eriksson; Pål Stenmark; Annika Jenmalm-Jensen; Thomas Helleday

doi:10.1039/C7OB02069D

Novel spirocyclic systems via multicomponent aza-Diels–Alder reaction†

Sabin Llona-Minguez,

*^a Adam Throup,

^a Emilie Steiner,^b Molly Lightowler,^a Sandra Van der Haegen,^a Evert Homan,

^a Lars Eriksson,^c Pål Stenmark,^d Annika Jenmalm-Jensen^e and Thomas Helleday^a

Author affiliations

* Corresponding authors

^a Division of Translational Medicine and Chemical Biology, Department of Medical Biochemistry and Biophysics, Karolinska Institute, Stockholm, Sweden
E-mail: sabin.llona.minguez@scilifelab.se

^b Division of Molecular Structural Biology, Department of Medical Biochemistry and Biophysics, Karolinska Institute, Stockholm, SE-171 77, Sweden

^c Department of Materials and Environmental Chemistry, Stockholm University, Stockholm, Sweden

^d Department of Biochemistry and Biophysics, Stockholm University, Stockholm, Sweden

^e Chemical Biology Consortium Sweden, Division of Translational Medicine and Chemical Biology, Department of Medical Biochemistry and Biophysics, Karolinska Institute, Stockholm, Sweden

Abstract

Here we present a two-step diastereoselective methodology building on a multicomponent aza-Diels–Alder reaction. Using previously unexplored cyclic ketones, heterocyclic amines and cyclopentadiene derivatives, we obtained novel spiro-heterocyclic frameworks at the interphase between “drug-like” molecules and natural products.

Organic & Biomolecular Chemistry

Novel spirocyclic systems via multicomponent aza-Diels–Alder reaction†

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