Abstract
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·H2O-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.
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