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 |
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| container_end_page | 8158 |
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| container_issue | 21 |
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| container_title | Journal of organic chemistry |
| container_volume | 71 |
| creator | Wehlan, Hermut Jezek, Eva Lebrasseur, Nathalie Pavé, Grégoire Roulland, Emmanuel White, Andrew J. P Burrows, Jeremy N Barrett, Anthony G. M |
| description | 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. |
| doi_str_mv | 10.1021/jo0613378 |
| format | Article |
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| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Chemical Sciences Chemistry Exact sciences and technology Indoles - chemical synthesis Naphthoquinones - chemical synthesis Organic chemistry |
| title | Studies on the Total Synthesis of Lactonamycin: Synthesis of the CDEF Ring System |
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