title: Multigram Synthesis of 1-O-Acetyl-3-O-(4-methoxybenzyl)-4-N-(9-fluorenylmethoxycarbonyl)-4-N-methyl-L-pyrrolosamine.
abstract: 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 theN,N-dimethyl-L-pyrrolosamine residues found within the antiproliferative bacterial metabolites (-)-lomaiviticins A and B (1and2, respectively), is reported. The synthetic route to7proceeds in eight steps and 13% overall yield from (E)-crotyl alcohol. The protected carbohydrate7is envisioned to be a useful derivative for syntheses of1and2.
authors.affiliation: Department of Chemistry, Yale University.
authors.forename: Matthew
authors.initials: M
authors.lastname: Burk
authors.affiliation: Department of Chemistry, Yale University.
authors.forename: Nolan
authors.initials: N
authors.lastname: Wilson
authors.affiliation: Department of Chemistry, Yale University.
authors.forename: Seth B
authors.initials: SB
authors.lastname: Herzon
keywords: carbohydrate; lomaiviticin; natural products; synthesis