Stylocheilamide, an unusual constituent of the sea hare Stylocheilus longicauda

Journal of the American Chemical Society
1978.0

Abstract

From the sea hare Stylocheilus longicauda we have isolated, in addition to the previously reported aplysiatoxins (1, 2), a novel nontoxic amide of composition C₂₈H₄₄ClNO₆. Stylocheilamide (3) is a tertiary amide constructed of a methoxyolefinic C₁₄ acid and a methyl(2-chloro-3-cyclohexyl-2-propenyl)amine. The highly functionalized carbocyclic ring gives rise to a related compound 4, differing only by the elements of HOAc. The structures have been elucidated by spectral analysis and chemical degradation. A key degradation product (8) was crystalline and its structure was determined by X-ray diffraction.

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