title: Copper-catalyzed diastereoselective arylation of tryptophan derivatives: total synthesis of (+)-naseseazines A and B.
abstract: A copper-catalyzed arylation of tryptophan derivatives is reported. The reaction proceeds with high site- and diastereoselectivity to provide aryl pyrroloindoline products in one step from simple starting materials. The utility of this transformation is highlighted in the five-step syntheses of the natural products (+)-naseseazine A and B.
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
authors.forename: Madeleine E
authors.initials: ME
authors.lastname: Kieffer
authors.forename: Kangway V
authors.initials: KV
authors.lastname: Chuang
authors.forename: Sarah E
authors.initials: SE
authors.lastname: Reisman
mesh_terms: D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D003300:Copper / Q000737:chemistry*; D054659:Diketopiperazines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry*
chemical_list: D054659:Diketopiperazines; C543447:naseseazine A; C543448:naseseazine B; D003300:Copper; D014364:Tryptophan
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