N-Oxide Route to the Marine Natural Product Cyanogramide D

Dustin M. Sarnes; Valentina Struck; Peter G. Jones; Thomas Lindel

doi:10.1055/a-2202-7145

Synthesis, Table of Contents

Synthesis 2024; 56(03): 408-417
DOI: 10.1055/a-2202-7145

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N-Oxide Route to the Marine Natural Product Cyanogramide D

Dustin M. Sarnes

^aTU Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig, Germany

,

Valentina Struck

^aTU Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig, Germany

,

Peter G. Jones

^bTU Braunschweig, Institute of Inorganic and Analytical Chemistry, Hagenring 30, 38106 Braunschweig, Germany

,

Thomas Lindel ∗

^aTU Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig, Germany

› Author Affiliations

Abstract

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Abstract

The first synthesis of the marine natural product cyanogramide D is reported. The key step is the acetylation of a β-carboline N-oxide, followed by acetyl migration. Since in this particular case it was not possible to incorporate the styryl side chain by Buchwald coupling, a phenylethanolamine side chain was attached, which was dehydrated with Martin’s sulfurane after assembly of the tetracycle. Pentacyclic products were obtained under Appel conditions. The synthesis will facilitate the exploration of the biomimetic oxidative spirocyclization of cyanogramide D to the spirooxindole cyanogramide.

Key words

natural products - alkaloids - dehydration - heterocycles - ketene aminals - total synthesis

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References

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