Chemoselective introduction of acetylene into hindered carbonyl group using alkynyltrifluoroborate, a solution as one step to (-)-tetrodotoxin

Article abstract of DOI:10.1016/S0040-4020(01)81827-5

Optically active cyclohexane moiety precursor for tetrodotoxin molecule was synthesized by Diels-Alder cycloaddition between a bromo derivative of levoglucosenone and Danishefsky type diene. The unstable product, bromo-ketone, was converted into vinylphos