Synthesis of the B-seco limonoid core scaffold

Synthesis 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–C...

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Bibliographic Details
Main Authors: Hanna Bruss, Hannah Schuster, Rémi Martinez, Markus Kaiser, Andrey P. Antonchick, Herbert Waldmann
Format: Article
Language:English
Published: Beilstein-Institut 2014-01-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
B-seco limonoids
biology oriented synthesis
Ireland–Claisen rearrangement
natural products
tetranortriterpenoids
Online Access:https://doi.org/10.3762/bjoc.10.15
Description
Summary: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.
ISSN:1860-5397

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