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Tandem single-step construction of chiral hexahydrophenanthrenes: a concise route to (+)-ferruginol
H Nagata1, N Miyazawa, K Ogasawara
1Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan.
Organic Letters
|June 19, 2001
Abstract:
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.