Trimethylsilylethynylmagnesium bromide

To a mixture of Co(acac)j (7.13 mg, 0.02 mmol) and l-(chloromethyl)-4-methylbenzene (151) (140mg, 1.00 mmol) in THF (0.5 ml) kept at 0°C, was added dropwise a solution of 2-trimethylsilylethynylmagnesium bromide (1.5 mmol) in THF (3.5 ml). The resulting mixture was warmed to room temperature and stirred for 10 h. After addition of saturated aqueous NH4CI solution, the usual workup gave a residue that was purified by silica gel column chromatography to provide 162 mg (80%) of 152 (Scheme 5.32) [100],... 

Aldol condensation of an acetyl iron anion with aldehyde-sugar derivatives (e.g. 36) and decomplexation of the iron led to chain-extended deoxy-uronic adds (e.g. 37 and its C-5 epimer), while addition of 2-trimethylsilylethynylmagnesium bromide to the 6-aldehyde derived from methyl 2,3,4-tri-O-benzyl-P-D-glucopyr-anoside followed by a multi-step procedure has afforded the amino-uronic add 38, the a-amino-acid on which miharamydn A is based. 

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