title: A chemical synthesis of 11-methoxy mitragynine pseudoindoxyl featuring the interrupted Ugi reaction.
abstract: A synthesis of 11-methoxy mitragynine pseudoindoxyl, a new member of the mitragynine class of opioid agonists, from a derivative of the Geissman-Waiss lactone is described. An internal attack of an electron-rich aromatic ring on an electrophilic nitrilium ion and a late-stage construction of the functionalized piperidine ring by the method of reductive cyclization are the pivotal transformations; both ring annulations proceed in a highly diastereoselective fashion. The construction of substituted indoxyl frameworks by the interrupted Ugi method offers an attractive alternative to the strategy of oxidatively rearranging indoles.
authors.affiliation: Department of Chemistry, Princeton University, Frick Chemistry Laboratory, Princeton, New Jersey 08544, USA. ; Tel: +1-609-258-8135.
authors.forename: Jimin
authors.initials: J
authors.lastname: Kim
authors.forename: John S
authors.initials: JS
authors.lastname: Schneekloth
authors.forename: Erik J
authors.initials: EJ
authors.lastname: Sorensen