Synthesis of Oxabicyclo[3.2.1]octan-3-ol Scaffold via Burgess Reagent Mediated Cyclodehydration of δ-Diols under Acidic Conditions

Mohamed F Elmansy; Jose Ricardo D Dos Remedios; Richard B Silverman

doi:10.1021/acs.orglett.4c04473

Synthesis of Oxabicyclo[3.2.1]octan-3-ol Scaffold via Burgess Reagent Mediated Cyclodehydration of δ-Diols under Acidic Conditions

Org Lett. 2025 Jan 6. doi: 10.1021/acs.orglett.4c04473. Online ahead of print.

Authors

Mohamed F Elmansy^{1

2}, Jose Ricardo D Dos Remedios¹, Richard B Silverman^{1

3}

Affiliations

¹ Department of Chemistry, Department of Molecular Biosciences, Chemistry of Life Processes Institute, Center for Developmental Therapeutics, Northwestern University, Evanston, Illinois 60208-3113, United States.
² Organometallic and Organometalloid Chemistry Department, National Research Centre, 12622 Cairo, Egypt.
³ Department of Pharmacology, Feinberg School of Medicine, Northwestern University, Chicago, Illinois 60611, United States.

PMID: 39761354
DOI: 10.1021/acs.orglett.4c04473

Abstract

Dehydrative cyclization of δ-diols was achieved by using the Burgess reagent under mild conditions to furnish a novel oxabicyclo[3.2.1]octan-3-ol scaffold. The stereochemistry of the generated oxabicyclic compounds was assigned based on single X-ray crystallography and 2D-NMR experiments.