TY - JOUR
T1 - Ten New Rearranged Spongian Diterpenes from two Dysidea Species
AU - Carmely, Shmuel
AU - Kashman, Yoel
AU - Cojocaru, Miriam
AU - Loya, Yossi
PY - 1988/9/1
Y1 - 1988/9/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0001557162&partnerID=8YFLogxK
U2 - 10.1021/jo00255a026
DO - 10.1021/jo00255a026
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AN - SCOPUS:0001557162
SN - 0022-3263
VL - 53
SP - 4801
EP - 4807
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 20
ER -