1007389-38-9Relevant academic research and scientific papers
Novel protoilludane lead structure for veterinary antibiotics: Total synthesis of pasteurestins A and B and assignment of their configurations
Koegl, Marion,Brecker, Lothar,Warrass, Ralf,Mulzer, Johann
experimental part, p. 2714 - 2730 (2009/04/07)
Two novel protoilludane sesquiterpenoids, named pasteurestins A and B (1 and 2), were disclosed in a recent patent. These compounds were reported to exhibit strong and selective activity against some Mannheimia haemolytica strains, pathogen causatives for bovine respiratory disease. These properties qualified 1 and 2 as potential lead structures for new veterinary antibiotics; however, neither the absolute nor the relative configurations had been determined, nor were the compounds available any longer. We thus developed total syntheses of 1 and 2 and clarified their structures and their biological profiles. Key steps were two [2+2+2] CpCo(CO)2-mediated Vollhardt cycloadditions in both syntheses, and a tin-mediated asymmetric Reformatsky-type condensation in the synthesis of 2 with a temperature-dependent product distribution. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
