title: Total synthesis of (±)-communesin F via a cycloaddition with indol-2-one.
abstract: A concise total synthesis of (±)-communesin F has been completed in 15 linear steps from 4-bromotryptophol in an overall yield of 6.7%. A key step features the cycloaddition of indol-2-one with 3-(2-azidoethyl)-4-bromoindole and facilitates the rapid construction of the lower aminal-containing tetracyclic core of the natural product.
authors.affiliation: Department of Chemistry, Pennsylvania State University, University Park, Pennsylvania 16802, USA.
authors.forename: Johannes
authors.initials: J
authors.lastname: Belmar
authors.forename: Raymond L
authors.initials: RL
authors.lastname: Funk
mesh_terms: D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; D007211:Indoles; C522025:communesin F