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Synthesis of the B-seco limonoid core scaffold.

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.

SUBMITTER: Bruss H

PROVIDER: S-EPMC3943702 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature

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Synthesis of the B-seco limonoid core scaffold.

Bruss Hanna H Schuster Hannah H Martinez Rémi R Kaiser Markus M Antonchick Andrey P AP Waldmann Herbert H

Beilstein journal of organic chemistry 20140116

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. ...[more]

PMID: 24605139

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