Chemistry of Puupehenone: 1,6-Conjugate Addition to Its Quinone−Methide System
- 31 October 1998
- journal article
- review article
- Published by American Chemical Society (ACS) in Journal of Natural Products
- Vol. 61 (12) , 1502-1508
- https://doi.org/10.1021/np9802062
Abstract
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.Keywords
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