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분자활성 촉매반응 연구단
분자활성 촉매반응 연구단
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Biosynthetically Inspired Syntheses of Secu′amamine A and Fluvirosaones A and B

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Title
Biosynthetically Inspired Syntheses of Secu′amamine A and Fluvirosaones A and B
Author(s)
Sanghyeon Lee; Gyumin Kang; Garam Chung; Dongwook Kim; Hee-Yoon Lee; Sunkyu Han
Publication Date
2020-04
Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.59, no.17, pp.6894 - 6901
Publisher
WILEY-V C H VERLAG GMBH
Abstract
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, WeinheimPresented here is a concise synthesis of secu′amamine A, and fluvirosaones A and B from readily available allosecurinine and viroallosecurinine. The key C2-enamine derivative of (viro)allosecurinine, the presumed biosynthetic precursors of these natural products, was accessed, for the first time, by a VO(acac)2-mediated regioselective Polonovski reaction. Formal hydration and 1,2-amine shift of this pluripotent enamine compound afforded secu′amamine A. Formal oxidative [3+2] cycloaddition reaction between this enamine and TMS-substituted methallyl iodide reagent paved the way to the precursors of fluvirosaones A and B. The relative stereochemistry at the C2 position of these advanced intermediates governs the fate of 1,2-amine shift leading to fluvirosaones A and B. The syntheses of potential biosynthetic precursors and investigations of their chemical reactivities have provided insights regarding the biogenesis of these natural products
URI
https://pr.ibs.re.kr/handle/8788114/7134
ISSN
1433-7851
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
Files in This Item:
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