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Enantiospecific Strategy Towards Oxygen‐Bridged Terpenoids: Tandem Transannular‐Cyclization and Ring‐Contraction Processes
Author(s) -
Rosales Antonio,
Estévez Rosa E.,
Cuerva Juan M.,
Oltra J. Enrique
Publication year - 2004
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200461210
Subject(s) - structural rigidity , rigidity (electromagnetism) , chemistry , contraction (grammar) , tandem , molecule , stereochemistry , terpenoid , oxygen , combinatorial chemistry , organic chemistry , materials science , mathematics , biology , geometry , composite material , endocrinology
From conformational flexibility to rigidity : The straightforward synthesis of rigid molecules with a transannular oxygen bridge starting from flexible germacrolides, which are easily obtained from renewable sources, is described (see scheme). Transannular cyclization of medium‐sized rings enhances molecular rigidity and structural complexity, two properties often associated with biological activity in small molecules.