Formation of benzo[b]fluorenes and the benzo[a]fluorene core of the fluostatins by cyclization of diaryldiynones.
[figure: see text] Thermal cyclization of 1-[2-(trimethylsilylethynyl)phenyl]-3-arylpropinones was expected to give benzo[b]fluorenones. However, benzo[a]-fluorenones were also formed as a result of a new rearrangement. These tetracycles possess the core structure of the fluostatins and isoprekinamycin.
Atienza
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Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain.
Mateo
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de Frutos
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Echavarren
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D000480:Alkynes / Q000138:chemical synthesis*; D005449:Fluorenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007202:Indicators and Reagents; D008968:Molecular Conformation; D015394:Molecular Structure; D011500:Protein Synthesis Inhibitors / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship
D000480:Alkynes; D005449:Fluorenes; D007202:Indicators and Reagents; D011500:Protein Synthesis Inhibitors; C041511:benzo(a)fluorene; C006703:benzo(b)fluoranthene