An improved synthesis of benzocycloalkanone derivatives.
A convenient and improved annulation method for the synthesis of bicyclic ketones was developed. A 2,2-dimethyl-6-(2-phenylsulfonyl)ethylcyclohexanone was converted into a sulfonylester by the addition of ethyl acetate and subsequent dehydration. A Dieckmann type condensation of the sulfonylester followed by desulfonylation afforded the 8,8-dimethyl-1,2,3,4,5,6,7,8-octahydronaphthalene-2-one in good yield. This annulation method was also applicable for the synthesis of the benzocyclooctanone derivative.
Wada
Akimori
A
Kobe Pharmaceutical University, 4-19-1 Motoyamakita-machi, Higashinada-ku, Kobe 658-8558, Japan. a-wada@kobepharma-u.ac.jp
Sawada
Kyoko
K
Ono
Naomi
N
Ito
Masayoshi
M
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D003500:Cyclization; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D011487:Protein Conformation; D012160:Retina / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D017550:Spectroscopy, Fourier Transform Infrared; D013450:Sulfones / Q000737:chemistry
D001643:Bridged Bicyclo Compounds; D007202:Indicators and Reagents; D013450:Sulfones