Journal
TETRAHEDRON LETTERS
Volume 57, Issue 46, Pages 5062-5064Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2016.10.007
Keywords
Photoredox catalysis; Visible light; Polonovski; Quinolizidine; Alkaloid
Categories
Funding
- Research Corporation for Science Advancement
- Hendrix College's Odyssey Program
- National Science Foundation [1040470]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1040470] Funding Source: National Science Foundation
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Quinolizidine alkaloids epi-cermizine C and epimyrtine were synthesized from a common intermediate in 5-6 steps from commercially available materials. The key step involved an allylsilane cyclization with an iminium ion formed by oxidation of a tertiary amine. Oxidative annulation was promoted either catalytically by visible light photoredox catalysis or by stoichiometric Polonovski-Potier conditions. There was a modest difference in diastereoselectivity between the two methods, with photoredox providing the key quinolizidine intermediate in 4.7:1 dr versus 2:1 dr for the Polonovski route. (C) 2016 Elsevier Ltd. All rights reserved.
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