1397290-00-4Relevant academic research and scientific papers
Highly efficient synthesis of the tricyclic core of taxol by cascade metathesis
Letort, Aurelien,Aouzal, Remi,Ma, Cong,Long, De-Liang,Prunet, Joelle
, p. 3300 - 3303 (2014)
An efficient enantioselective synthesis of the ABC tricyclic core of the anticancer drug Taxol is reported. The key step of this synthesis is a cascade metathesis reaction, which leads in one operation to the required tricycle if appropriate fine-tuning o
Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives
Ma, Cong,Letort, Aurélien,Aouzal, Rémi,Wilkes, Antonia,Maiti, Gourhari,Farrugia, Louis J.,Ricard, Louis,Prunet, Jo?lle
, p. 6891 - 6898 (2016)
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.
An aprotic Tamao oxidation/syn-selective tautomerization reaction for the efficient synthesis of the C(1)-C(9) fragment of fludelone
Harrison, Tyler J.,Rabbat, Philippe M.A.,Leighton, James L.
supporting information, p. 4890 - 4893 (2013/01/15)
An efficient synthesis of the C(1)-C(9) fragment of fludelone has been developed. The key step is a tandem silylformylation-crotylsilylation/ Tamao oxidation sequence that establishes the C(5) ketone, the C(6), C(7), and C(8) stereocenters, and the C(9) alkene in a single operation from a readily accessed starting material. The stereochemical outcome at C(6) depends critically on the development of an aprotic Tamao oxidation, which leads to a reversal in the intrinsic diastereoselectivity observed using standard Tamao oxidation conditions.
