title: Exercising regiocontrol in palladium-catalyzed asymmetric prenylations and geranylation: unifying strategy toward flustramines A and B.
abstract: Pd-catalyzed asymmetric prenylation of oxindoles to afford selectively either the prenyl or reverse-prenyl product has been demonstrated. Control of the regioselectivity in this transformation is governed by the choice of ligand, solvent, and halide additive. The resulting prenylated and reverse-prenylated products were transformed into ent-flustramides and ent-flustramines A and B. Additionally, control of the regio- and diastereoselectivity was obtained using π-geranylpalladium complexes.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
authors.forename: Barry M
authors.initials: BM
authors.lastname: Trost
authors.forename: Sushant
authors.initials: S
authors.lastname: Malhotra
authors.forename: Walter H
authors.initials: WH
authors.lastname: Chan
mesh_terms: D002384:Catalysis; D051228:Geranyltranstransferase / Q000737:chemistry; D026121:Indole Alkaloids / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D054876:Prenylation; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; D010165:Palladium; C041253:flustramine A; C041254:flustramine B; D051228:Geranyltranstransferase