A synthetic approach to nomofungin/communesin B.
[reaction: see text] A highly stereoselective intramolecular cycloaddition of an indole tethered to an aza-ortho-xylylene intermediate effects the rapid construction of a substantial portion of the ring system of the cytotoxic natural product communesin B. An analogous cycloaddition involving an ortho-quinone methide intermediate provides an adduct that clearly revealed that the structural assignment for nomofungin was in error.
Crawley
Seth L
SL
Department of Chemistry, Pennsylvania State University, University Park, Pennsylvania 16802, USA.
Funk
Raymond L
RL
D000470:Alkaloids / Q000138:chemical synthesis*; D003500:Cyclization; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D045563:Indolequinones / Q000737:chemistry*; D015394:Molecular Structure
D000470:Alkaloids; D004852:Epoxy Compounds; D045563:Indolequinones; C445785:nomofungin; C068040:quinone methide