Toxicols A-C and toxiusol - new bioactive hexaprenoid hydroquinones from Toxiclona toxius

Control of the Regio‐ and Diastereoselectivity for the Preparation of Highly Functionalized Terpenic Cyclopentanes through Radical Cyclization

“…These results may open the possibility of using these synthons as chiral building blocks that could help in the synthesis of complex structures such as toxicol A, [22] a hexaprenoid hydroquinone sulfate isolated from the Red Sea sponge Toxiclona toxius, which has been reported to inhibit the reverse transcriptase of human immune deficiency virus (HIV) and to be active against Candida albicans. This compound contains a five-membered ring (Cycle C) that might be obtained with suitable functionalization from commercially available sources by using this Ti III -mediated radical cyclization process (Scheme 10).…”

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“…Several of these compounds were found to possess antifungal activity against Candida albicans, and to inhibit HIV reverse transcriptase. 99 Specifically, toxiusol A had been shown to be a potent inhibitor of various viral reverse transcriptases. 100 Petrosynol and petrosolic acid (299,300), two polyacetylenes, were reported from the Red Sea sponge Petrosia sp.…”

Meroterpenes from Marine Invertebrates: Structures, Occurrence, and Ecological Implications

“…The sulfated compounds toxiusol ( 272 ), shaagrockol B ( 273 ), shaagrockol C ( 274 ), toxicol A ( 275 ), toxicol B ( 276 ), the p-hydroquinone derivative of compound 275 , and toxicol C ( 277 ), isolated from Toxiclona toxius [185,186], are of interest not only because of their structures but also because of their biological properties, which includes an important activity against human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT). The hydrolysis of compounds 272 and 274 yielded the corresponding hydroquinones designated as compounds 278 and 279 , and further oxidation of compound 276 afforded the corresponding p-quinone derivative.…”