Dragmacidin E synthesis studies. Preparation of a model cycloheptannelated indole fragment.
[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.
Feldman
Ken S
KS
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA. ksf@chem.psu.edu
Ngernmeesri
Paiboon
P
D002384:Catalysis; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure
D026121:Indole Alkaloids; C512386:dragmacidin E