Synthesis of Siphonazole B Through Domino Cycloisomerization-Oxazolonium Ion Rearrangements.

Filip Paulsen, Sebastian Clementson, Henrik von Wachenfeldt, Michał Antoszczak, Simon Fridolf, Daniel Strand

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Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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6 authors.

Filip PaulsenCentre for Analysis and Synthesis, Department of Chemistry, Lund University, Box 124, Lund, SE-221 00, Sweden.

Sebastian ClementsonCentre for Analysis and Synthesis, Department of Chemistry, Lund University, Box 124, Lund, SE-221 00, Sweden.

Henrik von WachenfeldtCentre for Analysis and Synthesis, Department of Chemistry, Lund University, Box 124, Lund, SE-221 00, Sweden.

Michał AntoszczakDepartment of Medical Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, Poznań, 61‒614, Poland.

Simon FridolfCentre for Analysis and Synthesis, Department of Chemistry, Lund University, Box 124, Lund, SE-221 00, Sweden.

Daniel StrandCentre for Analysis and Synthesis, Department of Chemistry, Lund University, Box 124, Lund, SE-221 00, Sweden.ORCID https://orcid.org/0000-0002-6113-4657

Funding

Carl Trygger Foundation CTS22:2252Carl Tryggers Stiftelse för Vetenskaplig Forskning CTS22:2252Kungliga Fysiografiska Sällskapet i LundVetenskapsrådet 2022-03176

6 · The paper itself

Abstract

4-Alkenyl- and 4-acyloxazoles represent important substructures across a diverse array of bioactive molecules. Practical methods to synthesize these motifs are, therefore, of considerable interest. Here, we develop a novel domino process wherein a cycloisomerization is followed by a 1,2-rearrangement via an oxazolonium ion to yield 4-alkenyloxazoles from an abundant β-chloro-N-benzyl propargylamine and acyl chlorides. The synthetic utility of the method is highlighted by its application to both oxazole units of siphonazole B, leading to a concise convergent total synthesis of this natural product.

Indexed as

domino reactionsnatural product synthesisoxidative amidationrearrangements

Identifiers

PMID40536015

DOI10.1002/chem.202501394

PMCPMC12271995

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