Ten New Rearranged Spongian Diterpenes from two Dysidea Species

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Abstract

Ten new rearranged spongian-type diterpenes have been isolated from two Red Sea Dysidea sponges. All new compounds embody either a perhydroazulene or a Δ5(10)-octalin system as the carbobicyclic portion and contain one of four heterocycles, that is, a disubstituted dihydrofuran, a trisubstituted γ-lactol, a trisubstituted δ-lactone, or a 2,7-dioxabicyclo[3.2.1]octane. Structures of all compounds were elucidated from spectral data, mainly by 1D and 2D NMR techniques, by mass spectra, and by comparison with other related known diterpenes. Four of the new compounds, shahamines B-E (4-7), were chemically correlated with the known aplyviolacene (macfarlandin E). CH4 versus NH3 CI mass spectra, performed on several of the new compounds, are discussed.

Original languageEnglish
Pages (from-to)4801-4807
Number of pages7
JournalJournal of Organic Chemistry
Volume53
Issue number20
DOIs
StatePublished - 1 Sep 1988

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