Studies on the Total Synthesis of Lactonamycin:  Synthesis of the CDEF Ring System

Studies on the Total Synthesis of Lactonamycin:  Synthesis of the CDEF Ring System

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 carri...

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Veröffentlicht in:Journal of organic chemistry 2006-10, Vol.71 (21), p.8151-8158
Hauptverfasser: Wehlan, Hermut, Jezek, Eva, Lebrasseur, Nathalie, Pavé, Grégoire, Roulland, Emmanuel, White, Andrew J. P, Burrows, Jeremy N, Barrett, Anthony G. M
Format: Artikel
Sprache:eng
Schlagworte:
Chemical Sciences
Chemistry
Exact sciences and technology
Indoles - chemical synthesis
Naphthoquinones - chemical synthesis
Organic chemistry
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0613378