Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives | Zendy

Ma Cong | Zendy; Letort Aurélien | Zendy; Aouzal Rémi | Zendy; Wilkes Antonia | Zendy; Maiti Gourhari | Zendy; Farrugia Louis J. | Zendy; Ricard Louis | Zendy; Prunet Joëlle | Zendy

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Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives

Author(s) -

Ma Cong,

Letort Aurélien,

Aouzal Rémi,

Wilkes Antonia,

Maiti Gourhari,

Farrugia Louis J.,

Ricard Louis,

Prunet Joëlle

Publication year - 2016

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201600592

Subject(s) - cascade , taxane , salt metathesis reaction , metathesis , combinatorial chemistry , chemistry , organic chemistry , biology , cancer , breast cancer , polymerization , genetics , polymer , chromatography

Tricyclic isotaxane and taxane derivatives have been synthesized by a very efficient cascade ring‐closing dienyne metathesis (RCDEYM) reaction, which formed the A and B rings in one operation. When the alkyne is present at C13 (with no neighboring gem ‐dimethyl group), the RCEDYM reaction leads to 14,15‐isotaxanes 16 a , b and 18 b with the gem ‐dimethyl group on the A ring. If the alkyne is at the C11 position (and thus flanked by a gem ‐dimethyl group), RCEDYM reaction only proceeds in the presence of a trisubstituted olefin at C13, which disfavors the competing diene ring‐closing metathesis reaction, to give the tricyclic core of Taxol 44 .

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