The synthesis, structural characterisation, and chemoselective manipulation of certain functionalised cyclic sulfates derived from chiral, non-racemic, and polysubstituted bicyclo[2.2.2]octane-2,3-diols

Martin G. Banwell, Antony L. Crisp, Bo Ra Lee, Ping Lan, Hannah E. Bollard, Jas S. Ward, Anthony C. Willis

Research output: Contribution to journalArticlepeer-review

Abstract

Certain cyclic sulfates (e.g. 23) together with various of their precursor sulfites (e.g. 21 and 22) have been prepared from the corresponding chiral, non-racemic bicyclo[2.2.2]octane-2,3-diols (e.g. 20). Such diols are obtained by engaging the corresponding enzymatically derived and enantiomerically enriched or homochiral cis-1,2-dihydrocatechol (e.g. 10) or certain derivatives in either inter- or intra-molecular Diels–Alder cycloaddition reactions. Other functionalities present within the title compounds can be chemoselectively manipulated without adversely affecting the associated sulfate residues.

Original languageEnglish
Pages (from-to)640-651
Number of pages12
JournalAustralian Journal of Chemistry
Volume74
Issue number9
DOIs
Publication statusPublished - 28 Jul 2021
Externally publishedYes

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