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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Formal Synthesis of Fostriecin via Asymmetric Alcohol-Mediated Carbonyl Allylation
Dana E Pfaffinger1, Michael J Krische1
1Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, United States.
Abstract:
A formal synthesis of fostriecin via convergent assembly of two fragments prepared via asymmetric alcohol-mediated C-C coupling is described. One fragment is made by the enantioselective iridium-catalyzed allylation of an allylic alcohol mediated by allyl acetate. The other fragment is made via enantioselective ruthenium-catalyzed reductive syn-(α-alkoxy)allylation of an aldehyde mediated by an alkoxyallene (where 2-propanol is the hydrogen source), representing the first use of this method in target-oriented synthesis. Metathetic fragment union enables interception of a late-stage compound that previously required a 25 step (LLS) synthesis in only 7 steps (LLS).
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