title: Total synthesis of (±)-cortistatin J from furan.
abstract: A concise, diastereoselective total synthesis of (±)-cortistatin J has been completed in 20 steps from furan. Key steps include an intramolecular [4 + 3] cyclization of a disubstituted furan with a (Z)-2-(trialkylsilyloxy)-2-enal to construct the tetracyclic core and a (Z)-vinylsilane/iminium ion cyclization to form the A ring.
authors.affiliation: Department of Chemistry, Pennsylvania State University, University Park, Pennsylvania 16802, United States.
authors.forename: Mark G
authors.initials: MG
authors.lastname: Nilson
authors.forename: Raymond L
authors.initials: RL
authors.lastname: Funk
mesh_terms: D000818:Animals; D003500:Cyclization; D005663:Furans / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D007546:Isoquinolines / Q000138:chemical synthesis*; D011161:Porifera / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D005663:Furans; D006576:Heterocyclic Compounds, 4 or More Rings; D007546:Isoquinolines; C545305:cortistatin J; C039281:furan