Clionamide, a major metabolite of the sponge Clionacelata Grant

Abstract

Clionamide, the major metabolite of the burrowing sponge Cliona celata, has been isolated. The structure of clionamide (1) was shown to be (2S)-N-((1E)-5,6,7-trihydroxystyr-1-yl)-2-amino-3-(6-bromoindol-3-yl)propionamide by spectral analysis and by interconversion to its tetracetyl derivative 2. The structure of 2 was determined from spectral data and extensive chemical degradation and was confirmed by the synthesis of its ultimate hydrogenation product, N-(5,6,7-triacetoxypheneth-1-yl)-2-acetamido-3-(indol-3-yl)propionamide (11).