title: Enantioselective Model Synthesis and Progress toward the Putative Structure of Yuremamine.
abstract: An enantioselective model synthesis of the 2,3-dihydro-1H-pyrrolo[1,2-a]indole core of the putative structure of yuremamine is reported in 39% overall yield and 96% ee over five steps. The model synthesis leverages enantioselective, rhodium-catalyzed hydroacylation of an N-vinylindole-2-carboxaldehyde as the key step in the installation of the stereochemical triad. An enantioselective synthesis of a densely functionalized dihydropyrroloindolone that maps onto the putative structure of yuremamine is demonstrated in 26% yield and 97% ee over eight steps.
authors: Department of Chemistry, Iowa State University , Ames, Iowa 50011, United States.
authors: Avipsa
authors: A
authors: Ghosh
authors: Department of Chemistry, Iowa State University , Ames, Iowa 50011, United States.
authors: David T
authors: DT
authors: Bainbridge
authors: Department of Chemistry, Iowa State University , Ames, Iowa 50011, United States.
authors: Levi M
authors: LM
authors: Stanley
mesh_terms: D066241:Carbon-13 Magnetic Resonance Spectroscopy; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry*; D066244:Proton Magnetic Resonance Spectroscopy; D012238:Rhodium / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
chemical_list: D007211:Indoles; D010936:Plant Extracts; C507332:Yuremamine; D012238:Rhodium