Synthesis of the B-seco limonoid core scaffold
Hanna Bruss1, Hannah Schuster1, Rémi Martinez2
1Abteilung Chemische Biologie, Max-Planck-Institut für Molekulare Physiologie, Otto-Hahn-Straße 11, 44227 Dortmund, Germany ; Fakultät für Chemie und Chemische Biologie, Technische Universität Dortmund, Otto-Hahn-Straße 6, 44227 Dortmund, Germany.
Abstract:
Synthetic investigations towards the structurally complex and highly decorated framework of B-seco limonoid natural products by means of a [3,3]-sigmatropic rearrangement are described. Detailed model studies reveal, that an Ireland-Claisen rearrangement can be employed to construct the central C9-C10 bond thereby giving access to the B-seco limonoid scaffold. However, application of the developed strategy ended up failing in more complex and sterically demanding systems.
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