A concise formal synthesis of luotonin A
โ Scribed by Daire Osborne; Paul J Stevenson
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 59 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
N-Acetyl-2-azetine undergoes Lewis acid catalysed [4+2] cycloaddition fragmentation reactions with imines derived from aniline to give 2,3-disubstituted quinolines. This chemistry was extended to a 2-glyoxylate imine to give rapid access to an advanced precursor to the antitumour alkaloid luotonin A.
๐ SIMILAR VOLUMES
The synthesis of the cytotoxic alkaloid luotonin A (1), which has been shown to possess antileukemic activity, has been achieved. The key step in the synthesis is a Friedl~inder condensation between 2-aminobenzaldehyde and dione 5.
ยฑ)-Methylenolactocin was prepared in five steps involving an indium-mediated allylation reaction as the key step.