Studies on the total synthesis of lactonamycin: synthesis of the CDEF ring system

H Wehlan, E Jezek, N Lebrasseur, G Pavé…

文献索引：Wehlan, Hermut; Jezek, Eva; Lebrasseur, Nathalie; Pave, Gregoire; Roulland, Emmanuel; White, Andrew J. P.; Burrows, Jeremy N.; Barrett, Anthony G. M. Journal of Organic Chemistry, 2006 , vol. 71, # 21 p. 8151 - 8158

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被引用次数: 20

摘要

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 ...