Total synthesis of a novel macrotetrolide |
| |
Authors: | Ludovic Coutable Christine Saluzzo |
| |
Institution: | a UCO2M, UMR 6011, Université du Maine, Avenue O. Messiaen, 72085 Le Mans Cedex 09, France b LdOF, UMR 6010, Université du Maine, Avenue O. Messiaen, 72085 Le Mans Cedex 09, France |
| |
Abstract: | 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. |
| |
Keywords: | |
本文献已被 ScienceDirect 等数据库收录! |
|