Synthesis of (+/-)-secosyrin 1 and a formal synthesis of (-)-secosyrin 1
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Updated: Aug 26, 2026

Hierarchical and Programmable One-Pot Oligosaccharide Synthesis
Published on: September 6, 2019
Timothy J Donohoe1, John W Fisher, Paul J Edwards
1Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, UK. timothy.donohoe@chem.ox.ac.uk
Abstract:
[reaction: see text] A short synthesis of (+/-)-secosyrin 1 is presented that starts from an electron-deficient furan; reductive alkylation under Birch conditions gives rapid access to the natural product skeleton. Two aspects of stereoselectivity are explored, the first being directed dihydroxylation of a homoallylic alcohol. Second, the facial selectivity obtained during reduction of a highly substituted cyclic ketone was examined. Finally, our synthesis was rendered enantioselective by the reduction of a furan bearing a chiral auxiliary.
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