Synthesis of the aminocyclopentenediol fragment of queuosine by way of the stereoselective addition of an organometallic reagent to a N-t-butanesulfinyl glycosylamine

Floriane Heis; Estelle Gallienne; Olivier R Martin

doi:10.1039/d3ob01713c

Synthesis of the aminocyclopentenediol fragment of queuosine by way of the stereoselective addition of an organometallic reagent to a N-t-butanesulfinyl glycosylamine

Org Biomol Chem. 2023 Dec 20;22(1):106-113. doi: 10.1039/d3ob01713c.

Authors

Floriane Heis¹, Estelle Gallienne¹, Olivier R Martin¹

Affiliation

¹ Institute of Organic and Analytical Chemistry, UMR 7311, University of Orleans and CNRS, Rue de Chartres, 45067 Orleans, France. olivier.martin@univ-orleans.fr.

PMID: 38050471
DOI: 10.1039/d3ob01713c

Abstract

An innovative, concise synthesis of the aminocyclopentenediol fragment of queuosine is reported. The synthesis is based on the stereocontrolled addition of a vinylGrignard·LiCl reagent to a t-butanesulfinyl L-ribofuranosylamine, followed by dehydrodeoxygenation to generate a second vinyl group and ring-closing metathesis to form the five-membered ring scaffold of the natural product. This approach has the potential for the development of a larger scale synthesis.