Multigram Synthesis of 1-O-Acetyl-3-O-(4-methoxybenzyl)-4-N-(9-fluorenylmethoxycarbonyl)-4-N-methyl-L-pyrrolosamine

A synthesis of 1-O-acetyl-3-O-(4-methoxybenzyl)-4-N-(9-fluorenylmethoxycarbonyl)-4-N-methyl-L-pyrrolosamine (7), which constitutes a protected form of the N,N-dimethyl-L-pyrrolosamine residues found within the antiproliferative bacterial metabolites (-)-lomaiviticins A and B (1 and 2, respectively), is reported. The synthetic route to 7 proceeds in eight steps and 13% overall yield from (E)-crotyl alcohol. The protected carbohydrate 7 is envisioned to be a useful derivative for syntheses of 1 and 2.