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

GonzálezCantalapiedra Esther | Zendy; de Frutos Óscar | Zendy; Atienza Carmen | Zendy; Mateo Cristina | Zendy; Echavarren Antonio M. | Zendy

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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)

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