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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-...

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Detalles Bibliográficos
Autores principales: Hore, Ratul, Halder, Tapas, Pradhan, Anirban, Mukherjee, Souvik, Maity, Joykrishna
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
Descripción
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.