Marine terpenes and terpenoids. XIV. Absolute configuration and acid-catalyzed transformation of (-)-12,13-didehydrofurospongin-1 isolated from an Arabian Sea sponge, Fasciospongia cavernosa SCHMIDT

Article abstract of DOI:10.1248/cpb.40.599

Three furanoterpenes, one having a furanocyclohexane ring (1) and two methyl ethers (2 and 3), and 12,13-didehydrofurospongin-1 (4a) were isolated from the lipid extract of the sponge, Fasciospongia cavernosa SCHMIDT. The absolute configuration of 4a at C-11 was shown to be (S), opposite to that reported for furospongin-1 (5). Compound 4a was found to be quite labile in acidic media and was converted, at room temperature, to 1 (HClO₄ in dioxane) or to a mixture of 1, 2 and 3 (HClO₄ in MeOH). These results suggest that 1, 2 and 3 are at least partly artefacts formed from 4a during the isolation process.

Full text of DOI:10.1248/cpb.40.599

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