Total Synthesis and Configuration Assignment of (+)‐Myxoquaterine‐450

Myxoquaterines represent a recently discovered class of natural products with intriguing biological properties. They were isolated from Pendulasporacea albinea MSr 11954 and display a unique structure combining heterocyclic (pyrrole, oxazoline), hexaene, and 2-amino-1,3-diol subunits. We have now synthesized the first example of a myxoquaterine natural product, myxoquaterine-450, in a highly convergent fashion, in which the sensitive hexaene unit was established in the final stages of the synthesis (16 linear steps starting from l-serine). Comparison of the synthetic material with an authentic sample allowed to establish and confirm the constitution and configuration of the natural product.

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Publication Details

Journal
Angewandte Chemie International Edition
Published
2024-11-08
DOI
https://doi.org/10.1002/anie.202416941
Primary Topic
Chemical synthesis and alkaloids
Type
article
Field-Weighted Citation Impact
0.00

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article

Total Synthesis and Configuration Assignment of (+)‐Myxoquaterine‐450

Thorsten Bach, Alexander Popoff, Rolf Müller, Johanna Löhr et al.
Angewandte Chemie International Edition
Chemical synthesis and alkaloids
article

Total Synthesis and Configuration Assignment of (+)‐Myxoquaterine‐450

Thorsten Bach, Alexander Popoff, Rolf Müller, Johanna Löhr, Sabrina Ortmann
article en

Abstract

Myxoquaterines represent a recently discovered class of natural products with intriguing biological properties. They were isolated from Pendulasporacea albinea MSr 11954 and display a unique structure combining heterocyclic (pyrrole, oxazoline), hexaene, and 2-amino-1,3-diol subunits. We have now synthesized the first example of a myxoquaterine natural product, myxoquaterine-450, in a highly convergent fashion, in which the sensitive hexaene unit was established in the final stages of the synthesis (16 linear steps starting from l-serine). Comparison of the synthetic material with an authentic sample allowed to establish and confirm the constitution and configuration of the natural product.

Angewandte Chemie International EditionVol. 64(4)
Helmholtz Institute for Pharmaceutical Research Saarland (DE), Technical University of Munich (DE)
Deutsche Forschungsgemeinschaft
Openalex Percentile: Top 85%
Chemical synthesis and alkaloids
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