The facile first total synthesis of a deuterated analog of natural muricadienin

An efficient five-step synthesis of muricadienin-d(2) has been successfully developed for the first time. A partially deuterated naturally occurring acetogenin analog has been obtained in 58% yield via the Ti-catalyzed cross-cyclomagnesiation reaction of the oxygen-containing 1,2-dienes and terminal aliphatic 1,2-dienes with EtMgBr. Incorporation of two deuteriums at positions 14 and 17 occurs during the D2O treatment of the in situ generated magnesacyclopentane. (C) 2016 Elsevier Ltd. All rights reserved.