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Synthesis of the Benzo[ b ]fluorene Core of the Kinamycins by Arylalkyne–Allene and Arylalkyne–Alkyne Cycloadditions
Author(s) -
GonzálezCantalapiedra Esther,
de Frutos Óscar,
Atienza Carmen,
Mateo Cristina,
Echavarren Antonio M.
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500926
Subject(s) - allene , chemistry , alkyne , fluorene , stereochemistry , yield (engineering) , organic chemistry , catalysis , materials science , metallurgy , polymer
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‐11 H ‐benzo[ b ]fluoren‐11‐one in excellent yield.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)