Cargando…
Easy Access to Sauropunols A–D: Synthesis and Spectroscopy Correlation of Their Natural Methyl and Ethyl Glycosides
[Image: see text] 3,6-Anhydro-2-deoxy-hexofuranoside, the natural product core, is present in natural sauropunols (A–D) and in their natural methyl and ethyl glycosides, now, namely, sauropunol H and sauropunol F. The easily synthesized d-glucose-derived 3,6-anhydro-1,2-O-isopropylidene-5-O-benzoyl-...
Autores principales: | , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
|
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10601080/ https://www.ncbi.nlm.nih.gov/pubmed/37901566 http://dx.doi.org/10.1021/acsomega.3c05742 |
Sumario: | [Image: see text] 3,6-Anhydro-2-deoxy-hexofuranoside, the natural product core, is present in natural sauropunols (A–D) and in their natural methyl and ethyl glycosides, now, namely, sauropunol H and sauropunol F. The easily synthesized d-glucose-derived 3,6-anhydro-1,2-O-isopropylidene-5-O-benzoyl-α-d-glucofuranose was elaborated to final targets employing the TsOH·H(2)O-catalyzed glycosylation reaction with seven different alcohols, subsequent radical deoxygenation, and appropriate deprotection reactions involving mild conditions with excellent functional group tolerance. A short total synthesis of sauropunols (A–D), sauropunol H, and the first total synthesis of sauropunol F are reported herein. The correlation of spectroscopy data of sauropunol H and sauropunol F has been derived through these syntheses. |
---|