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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)