biostudies-literatureUnknown10Bruss HSynthetic 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.Beilstein journal of organic chemistry194-208https://www.ebi.ac.uk/biostudies/studies/S-EPMC3943702biostudies-literatureSynthesis of the B-seco limonoid core scaffold.PMC3943702Waldmann HBruss HSchuster HMartinez RAntonchick APKaiser MfalseSynthesis of the B-seco limonoid core scaffold.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.2014-01-01T00:00:00Z20142025-04-04T14:14:29.334Z2019-03-27T01:22:44ZS-EPMC39437022460513910.3762/bjoc.10.15