title: Total synthesis of echinopines A and B.
abstract: Echinopines A and B [(+)-1 and (+)-2], two naturally occurring compounds characterized with a unique [3.5.5.7] carbon framework, have been synthesized in both enantiomeric and racemic forms. Their total synthesis involves a novel intramolecular rhodium-catalyzed cyclopropanation (4 --> 16) and a samarium diiodide-mediated ring closure (3 --> 37).
authors.affiliation: Chemical Synthesis Laboratory@Biopolis, Institute of Chemical and Engineering Sciences, Agency for Science, Technology and Research, 11 Biopolis Way, The Helios Block, #03-08, Singapore 138667. kcn@scripps.edu
authors.forename: K C
authors.initials: KC
authors.lastname: Nicolaou
authors.forename: Hanfeng
authors.initials: H
authors.lastname: Ding
authors.forename: Jean-Alexandre
authors.initials: JA
authors.lastname: Richard
authors.forename: David Y-K
authors.initials: DY
authors.lastname: Chen
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001688:Biological Products; D004952:Esters; D012717:Sesquiterpenes; C527602:echinopine A; C527604:echinopine B