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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) - tricyclic , chemistry , ring closing metathesis , salt metathesis reaction , alkyne , metathesis , taxane , ring (chemistry) , stereochemistry , cascade reaction , diene , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , biology , natural rubber , cancer , breast cancer , polymerization , genetics , polymer
Abstract 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 .