- Titel
- Chemo-enzymatic total synthesis of the spirosorbicillinols
- Zitierfähige Url:
- https://nbn-resolving.org/urn:nbn:de:bsz:14-qucosa2-948718
- Quellenangabe
- Communications chemistry
Erscheinungsjahr: 2023
Jahrgang: 6
E-ISSN: 2399-3669
Artikelnummer: 187 - Erstveröffentlichung
- 2023
- Abstract (EN)
- The natural product class of the sorbicillinoids is composed of structurally diverse molecules with many strong, biomedically relevant biological activities. Owing to their complex structures, the synthesis of sorbicillinoids is a challenging task. Here we show the first total synthesis of the fungal sorbicillinoids spirosorbicillinols A–C. The convergent route comprises the chemo-enzymatic transformation of sorbicillin to the highly reactive sorbicillinol and the assembly of scytolide and isomers starting from shikimic and quinic acid analogs. The key step in the total synthesis is the fusion of both building blocks in a Diels-Alder cycloaddition leading to the straightforward formation of the characteristic sorbicillinoid bicyclo[2.2.2]octane backbone. This work provides unifying access to all natural spirosorbicillinols and unnatural diastereomers.
- Andere Ausgabe
- Link zum Artikel, der zuerst in der Zeitschrift „Communications chemistry” im Verlag Macmillan Publishers Limited erschienen ist.
DOI: 10.1038/s42004-023-00996-1 - Verweis
- Ergänzendes Material ist unter folgendem Link zu finden.
Link: https://www.nature.com/articles/s42004-023-00996-1#Sec8 - Freie Schlagwörter (EN)
- Biocatalysis, Natural product synthesis, Oxidoreductases
- Klassifikation (DDC)
- 540
- Verlag
- Macmillan Publishers Limited, part of Springer Nature, [London]
- Version / Begutachtungsstatus
- publizierte Version / Verlagsversion
- URN Qucosa
- urn:nbn:de:bsz:14-qucosa2-948718
- Veröffentlichungsdatum Qucosa
- 05.11.2025
- Dokumenttyp
- Artikel
- Sprache des Dokumentes
- Englisch
- Lizenz / Rechtehinweis
CC BY 4.0