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.
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Alkynes
Allenes
Cycloadditions
Natural products
Quinones
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container_end_page 1443
container_issue 6
container_start_page 1430
container_title European Journal of Organic Chemistry
container_volume 2006
creator González-Cantalapiedra, Esther
de Frutos, Óscar
Atienza, Carmen
Mateo, Cristina
Echavarren, Antonio M.
description 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)
doi_str_mv 10.1002/ejoc.200500926
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subjects Alkynes
Allenes
Cycloadditions
Natural products
Quinones
title Synthesis of the Benzo[b]fluorene Core of the Kinamycins by Arylalkyne-Allene and Arylalkyne-Alkyne Cycloadditions
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