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

Autor: Michels TD; Department of Chemistry, The University of California, Irvine, California 92697-2025, USA., Kier MJ, Kearney AM, Vanderwal CD
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2010 Jul 02; Vol. 12 (13), pp. 3093-5.
DOI: 10.1021/ol101035p
Abstrakt: 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.
Databáze: MEDLINE