Spongistatins: Biological activity and synthetic studies

Tetrahydrofuran-Containing Macrolides: A Fascinating Gift from the Deep Sea

“…Their relative stereochemistry and connectivity was described based on spectroscopic techniques, although absolute stereochemistry remains unknown. Unusual structural features of these natural products are the C(8−18) tricyclic core, based on [6,5] spiroketal and trans-bridged tetrahydropyran rings. In addition, they possess an exocyclic dienamide moiety (Figure 38).…”

“…A significant number of marine polyketide macrolides have been isolated in the last years from sponges, algae, dinoflagellate, and other marine invertebrates, characterized by their structural novelty. From a chemical structure point of view, marine polyketide macrolides are fascinating, many of them being highly oxygenated and stereochemically elaborate, such as, for instance, the oxazole containing polyketides kabiramide C, halichondramide, and ulapualide A or the complex polyketide family of the spongistatins (Figure ).…”

Structure and conformational analysis of spiroketals from 6-O-methyl-9(E)-hydroxyiminoerythronolide A

“…A previously mentioned example of a protein phosphatase inhibitor okadaic acid is a toxin associated with diarrheic shellfish poisoning [ 28 ]. Another example are structurally complex tubulin polymerization-inhibiting macrolides such as spongistatins, a family of compounds isolated from marine sponges, which display extraordinary antitumor activity [ 29 ]. At the same time, the spiroketal-containing integramycin acts as an HIV-1 protease inhibitor [ 27 ].…”