The highly diastereoselective addition of organometallic derivatives of trimethylsilylacetylen to N-Boc-O-Me-L-thyrosinal - Synthesis directed towards anisomycin

Abstract

Anisomycin analogue precursor was synthesised starting from a suitably protected α-amino aldehyde - tyrosine. The crucial step involves the addition of acetylenic reagent to N-Boc-O-methyl-L-tyrosinal in the presence of zinc(II) bromide, affording a syn-acetylenic adduct with high diastereoselectivity.