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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 
a   TU Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig, Germany
,
Valentina Struck
a   TU Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig, Germany
,
Peter G. Jones
b   TU Braunschweig, Institute of Inorganic and Analytical Chemistry, Hagenring 30, 38106 Braunschweig, Germany
,
Thomas Lindel  ∗
a   TU Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig, Germany
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2202-7145.
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Publication History

Received: 26 September 2023

Accepted after revision: 02 November 2023

Accepted Manuscript online:
02 November 2023

Article published online:
04 December 2023

© 2023. Thieme. All rights reserved

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