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

Rosselli Sergio | Zendy; Maggio Antonella | Zendy; Raccuglia Rosa Angela | Zendy; Bruno Maurizio | Zendy

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

Author(s) -

Rosselli Sergio,

Maggio Antonella,

Raccuglia Rosa Angela,

Bruno Maurizio

Publication year - 2003

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200300161

Subject(s) - chemistry , isomerization , absolute configuration , double bond , stereochemistry , absolute (philosophy) , organic chemistry , catalysis , philosophy , epistemology

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)

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