Rearrangement of Germacranolides. Synthesis and Absolute Configuration of Elemane and Heliangolane Derivatives from Cnicin

6533b858fe1ef96bd12b64d9

RESEARCH PRODUCT

Rearrangement of Germacranolides. Synthesis and Absolute Configuration of Elemane and Heliangolane Derivatives from Cnicin

Sergio Rosselli Antonella Maggio Maurizio Bruno Rosa Angela Raccuglia

subject

chemistry.chemical_classification chemistry.chemical_compound chemistry Double bond Centaurea paui Stereochemistry Organic Chemistry Absolute configuration Physical and Theoretical Chemistry Cnicin Isomerization Cope rearrangement

description

A study of the Cope rearrangement of 15-oxo-germacranolides to 15-oxo-elemanolides has been carried out. The synthesis of two natural elemanolides, isolated from Centaurea paui, and an efficent isomerization of the C-4/C-5 double bond of 15-oxo-germacranolides to form heliangolides are reported. The absolute configuration of all the compounds has been ascertained. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

year	journal	country	edition	language
2003-07-01	European Journal of Organic Chemistry

https://doi.org/10.1002/ejoc.200300161

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