A carcinogen with a bridged bay region: synthesis, X-ray structure, and biological activity of 15,16-dihydro-1,11-methanocyclopenta[a]phenanthren-17-one

Abstract

8DB)Suininary 15,lg-Dihydro-1,ll-methanocyclopenta [alphenanthren-1 ?' -one has been synthesised and its X-ray structure determined; although it has a bridged bay region, it is a carcinogen.

Potentially carcinogenic cyclopenta[a]phenanthrenes. Part 11. Synthesis of the 1-methyl, 1,11-methano, and 7,11-dimethyl derivatives of 15,16-dihydrocyclopenta[a]phenanthren-17-one

“…spectra, fluorescence, and R, values in several systems identical with those of the pure, analysed sample (see below). (8).-Methyl 4-0x0-4-o-tolylbutyrate (7) l6 (61 g), methyl bromoacetate (52 ml), zinc fillings (36 g), and a small crystal of iodine were heated together in dry ether (200 ml) under reflux. A vigorous reaction took place, after which reflux was maintained for 6 h. The cooled reaction mixture was added to an excess of ice and hydrochloric acid; the organic layer was separated and the aqueous layer was extracted twice with ether.…”