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Synthesis of Siphonazole B Through Domino Cycloisomerization-Oxazolonium Ion Rearrangements

Paulsen, Filip LU ; Clementson, Sebastian LU orcid ; von Wachenfeldt, Henrik LU ; Antoszczak, Michał ; Fridolf, Simon LU and Strand, Daniel LU (2025) In Chemistry – A European Journal 31(40). p.202501394-202501394
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. © 2025 The Author(s). Chemistry – A European Journal published by Wiley-VCH GmbH.
Abstract (Swedish)
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.
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author
; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
domino reactions, natural product synthesis, oxidative amidation, rearrangements
in
Chemistry – A European Journal
volume
31
issue
40
pages
202501394 - 202501394
publisher
Wiley-Blackwell
external identifiers
  • pmid:40536015
  • scopus:105009212201
DOI
10.1002/chem.202501394
language
English
LU publication?
yes
id
84e11b1a-cdbb-4cd4-8ae2-d0122bdd3be3
date added to LUP
2025-08-06 19:49:00
date last changed
2025-08-18 09:06:21
@article{84e11b1a-cdbb-4cd4-8ae2-d0122bdd3be3,
  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. © 2025 The Author(s). Chemistry – A European Journal published by Wiley-VCH GmbH.}},
  author       = {{Paulsen, Filip and Clementson, Sebastian and von Wachenfeldt, Henrik and Antoszczak, Michał and Fridolf, Simon and Strand, Daniel}},
  keywords     = {{domino reactions; natural product synthesis; oxidative amidation; rearrangements}},
  language     = {{eng}},
  number       = {{40}},
  pages        = {{202501394--202501394}},
  publisher    = {{Wiley-Blackwell}},
  series       = {{Chemistry – A European Journal}},
  title        = {{Synthesis of Siphonazole B Through Domino Cycloisomerization-Oxazolonium Ion Rearrangements}},
  url          = {{http://dx.doi.org/10.1002/chem.202501394}},
  doi          = {{10.1002/chem.202501394}},
  volume       = {{31}},
  year         = {{2025}},
}