1095268-29-3Relevant academic research and scientific papers
A general and highly efficient synthesis of novel nonactic acid analogues
Coutable, Ludovic,Saluzzo, Christine
, p. 3389 - 3396 (2008)
An efficient enantioselective synthesis of protected non-actic acid analogues, starting from an easily accessible β-keto ester, is described. The key steps of the strategy are asymmetric hydrogenation, chelation-controlled allylation, cis-selective etherification, and stereoselective reduction or alkylation of α-halo esters. Georg Thieme Verlag Stuttgart.
Total synthesis of a novel macrotetrolide
Coutable, Ludovic,Adil, Karim,Saluzzo, Christine
experimental part, p. 11296 - 11303 (2009/04/06)
The total synthesis of a novel macrotetrolide, an isobutyl nonactin analog, has been achieved in 15% yield by coupling both enantiomers of the corresponding nonactic acid analogs followed by macrolactonization. These building blocks were prepared starting from β-ketoester in nine steps and 34% overall yield, in an efficient and highly stereoselective sequence. The key steps of the strategy are asymmetric hydrogenation, chelation-controlled allylation, intramolecular haloetherification of bishomoallylic ether presenting a trisubstituted double bond deactivated by an ester, and finally a stereoselective reduction of α-bromoester.
