Metacycloprodigiosin, a tripyrrole pigment from Streptomyces longisporus ruber

Journal of the American Chemical Society
1969.0

Abstract

We have recently reported the structure and synthesis of undecylprodigiosin (11), a C-25 prodigiosin analog isolated from a strain of Streptomyces. At that time it was noted that another more complex C-25 prodigiosin-like pigment was formed concurrently with 11. In this communication we describe the isolation and structure determination of this product. Formulated as I, this new tripyrrole pigment incorporates the unusual structural feature of a meta-bridged pyrrole, the first such system to be observed in a natural product. We propose the trivial name metacycloprodigiosin for this new pigment (I), the synthesis of which is described in the accompanying report. In the accompanying communication we have reported the isolation and structure determination of metacycloprodigiosin (1), a tripyrrole pigment from Streptomyces. We now describe the synthesis of the racemic form of this pigment which confirms the structural assignment.

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