Work

A Practical and Flexible De Novo Synthesis of Deoxygenated Carbasugars and Their Cyclitol Epoxides

Year: 2026

Type: article

Abstract: Literature on carbasugar and cyclitol epoxide glycomimetics is largely biased towards fully hydroxylated cyclitol structures. Partially deoxygenated sugars of varying configuration are widespread in nature and merit translation into the corresponding carbasugars and cyclitol epoxides as well. For this purpose, we developed a de novo synthesis route comprising enantioselective Brown crotylation and ring‐closing metathesis as the key steps and enabling the synthesis of α‐ and β‐carba‐paratose, α‐ and β‐carba‐colitose as well as four configurational deoxycyclophellitol isosteres in a strategy that allows the synthesis of other configurational isomers.

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.70417

Authors: Yevhenii Radchenko, Nick D. F. Puijmbroeck, Sanne M. Verduin, Jeroen D. C. Codée, Herman S. Overkleeft

Institution: Leiden University

Language: English

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,330

Funder: European Research Council