Dimerization Strategies for the Synthesis of High-Order Securinega Alkaloids

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Title
Dimerization Strategies for the Synthesis of High-Order Securinega Alkaloids
Author(s)
Joonoh Park; Seongmin Jeon; Gyumin Kang; Jongsun Lee; Mu-Hyun Baik; Sunkyu Han
Publication Date
2019-02
Journal
JOURNAL OF ORGANIC CHEMISTRY, v.84, no.3, pp.1398 - 1406
Publisher
AMER CHEMICAL SOC
Abstract
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. Copyright © 2018 American Chemical Society.
URI
https://pr.ibs.re.kr/handle/8788114/5705
ISSN
0022-3263
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
Files in This Item:
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