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Concise formal synthesis of porothramycins A and B via Zincke pyridinium ring-opening/ring-closing cascade

Concise formal synthesis of porothramycins A and B via Zincke pyridinium ring-opening/ring-closing cascade

Organic Letters 12(13): 3093-3095

Short formal syntheses of the antitumor antibiotics porothramycins A and B from a commercially available ester of the unnatural amino acid 3-(3-pyridyl)alanine are presented. A rearrangement cascade that presumably involves a Zincke-type pyridinium ring-opening followed by cyclization of a pendant nucleophilic amide generates the salient pyrroline ring of the alkaloids.

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Accession: 052284135

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PMID: 20527899

DOI: 10.1021/ol101035p

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