Synthesis of the Benzo[b]fluorene Core of the Kinamycins by Arylalkyne-Allene and Arylalkyne-Alkyne Cycloadditions

Synthesis of the Benzo[b]fluorene Core of the Kinamycins by Arylalkyne-Allene and Arylalkyne-Alkyne Cycloadditions

Arylalkyne–allene and arylalkyne–alkyne cycloadditions yields benzo[a]fluorenones, which are related to the tetracyclic core of the kinamycins. In the arylalkyne–alkyne cycloadditions, we found a rearrangement that produces benzo[a]fluorenones, in addition to the expected benzo[b]fluorenones. This r...

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Veröffentlicht in:European Journal of Organic Chemistry 2006-03, Vol.2006 (6), p.1430-1443
Hauptverfasser: González-Cantalapiedra, Esther, de Frutos, Óscar, Atienza, Carmen, Mateo, Cristina, Echavarren, Antonio M.
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes
Allenes
Cycloadditions
Natural products
Quinones
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Zusammenfassung:Arylalkyne–allene and arylalkyne–alkyne cycloadditions yields benzo[a]fluorenones, which are related to the tetracyclic core of the kinamycins. In the arylalkyne–alkyne cycloadditions, we found a rearrangement that produces benzo[a]fluorenones, in addition to the expected benzo[b]fluorenones. This rearrangement could be suppressed in the presence of phenol, which allowed the synthesis of 4,9‐dimethoxy‐2‐methyl‐11H‐benzo[b]fluoren‐11‐one in excellent yield.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200500926