Dimerization Strategies for the Synthesis of High-Order Securinega Alkaloids

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We describe different modes of dimerization of various α′,γ-dioxyenone derivatives with potential applications to the synthesis of high-order securinega alkaloids. We learned that the relative stereochemical relationship between α′- and γ-hydroxyl groups of the α′,γ-dihydroxyenone derivative determines the mode of dimerization. While cis-α′,γ-dioxyenone 26 provided the Rauhut–Currier-type (RC-type) dimer 31 upon reaction with TBAF, trans-α′,γ-dihydroxyenone 34 afforded dimeric tetrahydrofuran derivative 41 under the same reaction conditions. We also noticed that the protection of the γ-hydroxyl group drastically changes the reaction outcomes. While cis-α′-oxy-γ-OPiv-enone 49 did not show any reactivity in the presence of TBAF, trans-α′-hydroxy-γ-OPiv-enone 45 produced the RC-type dimer 46 under the same reaction conditions. Computational analysis revealed the detailed mechanism of the latter transformation.
Publisher
AMER CHEMICAL SOC
Issue Date
2019-02
Language
English
Article Type
Article
Citation

JOURNAL OF ORGANIC CHEMISTRY, v.84, no.3, pp.1398 - 1406

ISSN
0022-3263
DOI
10.1021/acs.joc.8b02852
URI
http://hdl.handle.net/10203/250347
Appears in Collection
CH-Journal Papers(저널논문)
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