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- W2079728788 abstract "Eunicellane diterpenes with a C(7)=C(16) (Δ7,16; see 17 – 19), (Z)-C(7)=C(8) ((7Z)Δ7,8; see 20 – 23), and (Z)-C(6)=C(7) ((6Z)Δ6,7; see 10) bond, an uncommon feature in the case of extensive functionalization at the cyclohexane ring and the latter exhibiting uncommon configurations, were isolated from the gorgonian Eunicella cavolinii from Marseille (Figs. 5 and 2). The gorgonian Eunicella singularis (=Eunicella stricta) from the same area gave (7Z)Δ7,8, Δ7,16, and (6E)Δ6,7 analogs 24, 25, and 13, respectively (Fig. 5 and Scheme). The (6E)Δ6,7 moiety of 13 – characterized by a slow 180° conformational flipping (Fig. 3) that results in broadening of NMR signals – makes the macrocycle highly strained. This may explain the spontaneous conversion of 13 to the 6-methoxy-7-hydroxy derivative 14 in the presence of MeOH at −20° in the dark (Scheme). The isomeric, deacylated analogue 10 showed only little broadening of NMR signals and proved stable, in accordance with the less strained nature of this compound (Fig. 4)." @default.
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- W2079728788 date "2000-07-05" @default.
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- W2079728788 title "Configuration, Conformation, and Reactivity of Highly Functionalized Eunicellane Diterpenes Isolated from the Gorgonians Eunicella cavolinii and Eunicella singularis from Marseille" @default.
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