Base-mediated transformations of 3,5-dibromoverongiaquinol from the sponge Aplysina sp. to cavernicolins-1, -2 and a subereatensin analogue.
Treatment of 3,5-dibromoverongiaquinol (1) with NaHCO3-MeOH at room temperature gave cavernicolin-1 (2), cavernicolin-2 (3), the 4,7-dimethoxy analogue of subereatensin (4) and dimethyl ketal (5). These transformations may clarify the origin of the cavernicolins and subereatensin isolated from the extracts of some verongid sponges.
Laboratory of Marine Natural Products Chemistry, Pacific Institute of Bioorganic Chemistry of the Far-Eastern Branch of the Russian Academy of Sciences, Vladivostok 690022, Prospect 100-let Vladivostoku, 159, Russia. santalova@piboc.dvo.ru
Elena A
EA
Santalova
D000818:Animals; D007769:Lactams / Q000378:metabolism; D011161:Porifera / Q000378:metabolism*
D007769:Lactams