Studies in relation to biosynthesis—XLIV

Tetrahedron
1972.0

Abstract

The culture medium of Peniciflium brevi-compacrum Dierckx contains the neutral metabolites, brevianamides-A to -F. The structures of -A and -E*, based upon spectroscopic. biogenetic and degradative evidence, have been reported.' Preparative TLC of the residues from the crystallization of brevianamide-A yields -B, -C and -D in the pure state. High resolution mass-spectrometry shows them to have the formula C,,H,,N,O,, isomeric with brevianamide-A. Brevianamide-B is shown by interconversion with brevianamide-A to be a stereoisomer.Brevianamides-C and -D are shown to contain a 2'Gndoxylidenealkane chromophore and are the stereoisomers (1) and (2) respectively. For spectral comparisons the cis and tram isomers of 2,2dimethyl-l- (2'~indoxylidengnopane have been synthesized. Brevianamides-C and -D are obtained by irradiation with visible light of brevianamide-A.A NEW brevianamide (fj is shown to be identical with cycle-L-tryptophanyl+proline.lThe formula 23 in reference 2 was incorrectly printed and the correct formula is 13.

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