Synthesis of the trans-3, 4-dihydrodiol metabolites of the steroid-related carcinogen 15, 16-dihydrocyclopenta [a] phenanthren-17-one and its 11-methyl derivative

RG Harvey, RJ Young, C Cortez, H Lee…

Index: Harvey, Ronald G.; Young, Robert J.; Cortez, Cecilia; Lee, Hongmee; Luna, Ernestina Journal of Organic Chemistry, 1993 , vol. 58, # 2 p. 361 - 365

Full Text: HTML

Citation Number: 10

Abstract

0 P&C 0 0 centage of a product hydrogenated in the ring containing the methyl group (10) in addition to the 6, 7-dihydro compound 9. This secondary product proved difficult to remove at this stage, but it was readily separated from the product of the next step in the sequence. Oxidation of 9 with DDQ in moist acetic acid9 took place regiospecifically in the 17-position to yield the 17-keto derivative 11. Dehydrogenation of 11 over a 10% palladium-charcoal ...