Chemistry of puupehenone: 1,6-conjugate addition to its quinone-methide system

The marine natural product puupehenone (1), isolated in good yields from sp onges of the genus Hyrtios, has been shown to undergo stereospecific 1,6-co njugate addition to its quinone-methide system. Several nucleophilic agents such as hydrogen cyanide, Grignard reagents, and nitroalkanes were studied , producing structurally diverse compounds. This lead optimization study wa s initiated due to the bioactivity of puupehenone and its natural analogues , which includes numerous previous reports of potential anticancer and anti infective activity.