Studies on the Total Synthesis of Lactonamycin: Synthesis of the CDEF Ring System
The Journal of Organic Chemistry2006Vol. 71(21), pp. 8151–8158
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Hermut Wehlan, Eva Jezek, Nathalie Lebrasseur, G. Pave, Emmanuel Roulland, Andrew J. P. White, Jeremy N. Burrows, Anthony G. M. Barrett
Abstract
A concise and efficient synthesis of the tetracyclic CDEF ring system of lactonamycin (1) is described. The key step involved the Lewis acid mediated, intramolecular Friedel-Crafts acylation of carboxylic acid 6 to produce the tetracyclic CDEF core structure of target 1. The synthesis of 6 was carried out using a high-yielding Negishi coupling of benzyl bromide 7 with triflate 8, which was accessible in 11 steps and 31% overall yield on a multigram scale starting from trihydroxy acid 9.
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