Journal
TETRAHEDRON
Volume 72, Issue 38, Pages 5783-5787Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2016.08.005
Keywords
Allenes; Grignard reagents; Cross-cyclomagnesiation; Homogeneous catalysis; Acetogenins; Muricadienin
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Funding
- Russian Science Foundation [14-13-00263]
- Russian Foundation for Basic Research [15-33-20043, 14-03-97024]
- Grant of RF President [MD-6293.2016.3]
- Russian Science Foundation [14-13-00263] Funding Source: Russian Science Foundation
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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.
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