title: Dragmacidin E synthesis studies. Preparation of a model cycloheptannelated indole fragment.
abstract: [reaction: see text] The conversion of N-2,2-dichloropropionyl indole methyl ester into a tetracyclic cycloheptannelated indole model compound for the synthesis of dragmacidin E was accomplished in 10 steps. Key reactions include a Witkop cyclization to fashion a C-C bond at C(4) of the indole nucleus and a subsequent Dieckmann cyclization to deliver the desired cycloheptanoid ring.
authors.affiliation: Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA. ksf@chem.psu.edu
authors.forename: Ken S
authors.initials: KS
authors.lastname: Feldman
authors.forename: Paiboon
authors.initials: P
authors.lastname: Ngernmeesri
mesh_terms: D002384:Catalysis; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: D026121:Indole Alkaloids; C512386:dragmacidin E