Chemistry of puupehenone: 1,6-conjugate addition to its quinone-methide system.
The marine natural product puupehenone (1), isolated in good yields from sponges of the genus Hyrtios, has been shown to undergo stereospecific 1,6-conjugate 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 was initiated due to the bioactivity of puupehenone and its natural analogues, which includes numerous previous reports of potential anticancer and antiinfective activity.
Zjawiony
J K
JK
Department of Pharmacognosy, National Center for the Development of Natural Products, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, Mississippi 38677, USA.ricotta@olemiss.edu
Bartyzel
P
P
Hamann
M T
MT
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011161:Porifera / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry; D044004:Xanthones
D000970:Antineoplastic Agents; D012717:Sesquiterpenes; D044004:Xanthones; C053594:puupehenone