Biosynthetically Inspired Syntheses of Secu′amamine A and Fluvirosaones A and B

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Presented 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.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2020-04
Language
English
Article Type
Article
Citation

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.59, no.17, pp.6894 - 6901

ISSN
1433-7851
DOI
10.1002/anie.201916613
URI
http://hdl.handle.net/10203/273891
Appears in Collection
CH-Journal Papers(저널논문)
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