Tandem single-step construction of chiral hexahydrophenanthrenes: a concise route to (+)-ferruginol.
An efficient enantio- and diastereocontrolled construction of hydrophenanthrenes having either a quaternary or a tertiary benzylic stereogenic center has been developed by employing a tandem retro-aldol and intramolecular Friedel-Crafts alkylation sequence. Its application to a diastereocontrolled synthesis of an abietane diterpenoid (+)-ferruginol has also been demonstrated.
Nagata
H
H
Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan.
Miyazawa
N
N
Ogasawara
K
K
D045784:Abietanes; D000478:Alkylation; D004224:Diterpenes / Q000138:chemical synthesis*; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D013237:Stereoisomerism
D045784:Abietanes; D004224:Diterpenes; D007202:Indicators and Reagents; C431074:ferruginol