Tandem single-step construction of chiral hexahydrophenanthrenes: A concise route to (+)-ferruginol

Authors
Nagata, H Miyazawa, N Ogasawara, K
Citation
H. Nagata et al., Tandem single-step construction of chiral hexahydrophenanthrenes: A concise route to (+)-ferruginol, ORG LETT, 3(11), 2001, pp. 1737-1740
Citations number
17
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
11
Year of publication
2001
Pages
1737 - 1740
Database
ISI
SICI code
1523-7060(20010531)3:11<1737:TSCOCH>2.0.ZU;2-G
Abstract
An efficient enantio- and diastereocontrolled construction of hydrophenanth renes having either a quaternary or a tertiary benzylic stereogenic center has been developed by employing a tandem retro-aldol and intramolecular Fri edel-Crafts alkylation sequence, Its application to a diastereocontrolled s ynthesis of an abietane diterpenoid (+)-ferruginol has also been demonstrat ed.