Bogert-Cook Synthesis

M. T. Bogert, Science 77, 289 (1933); J. W. Cook, C. L. Hewett, J. Chem. Soc. 1933, 1098.

Condensation of β-phenylethylmagnesium bromide with cyclohexanones followed by cyclodehydration of the tertiary alcohol with concentrated sulfuric acid with formation of octahydro derivatives and a small amount of spiran:



L. F. Fieser, M. Fieser, Natural Products Related to Phenanthrene (New York, 1949) p 90; C. Schmidt et al., Can. J. Chem. 51, 3620 (1973). For a general approach to the synthesis of phenanthrenoid compounds, see D. A. Evans et al., J. Am. Chem. Soc. 99, 7083 (1977).