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Synthesis of the B-seco limonoid core scaffold

Hanna Bruss, Hannah Schuster, Rémi Martinez and 3 more

Beilstein Journal of Organic Chemistry · 2014

doi:10.3762/bjoc.10.15 (opens in a new tab)

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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.

Abstract licence: CC BY

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