Cneorins, cyclopropanes and propellanes : synthesis of windmill molecules

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dc.contributor Aalto-yliopisto fi
dc.contributor Aalto University en
dc.contributor.author Pihko, Ainoliisa
dc.date.accessioned 2012-02-17T07:00:14Z
dc.date.available 2012-02-17T07:00:14Z
dc.date.issued 2005-05-28
dc.identifier.isbn 951-22-7653-4
dc.identifier.issn 1236-2999
dc.identifier.uri https://aaltodoc.aalto.fi/handle/123456789/2569
dc.description.abstract Propellanes are molecules in which a tricyclic system is conjoined by a carbon–carbon single bond. They have been studied both theoretically and synthetically. Propellane structures are present in many different classes of natural products. Total syntheses of these natural products are reviewed. Cneorin C has been isolated from the xerophytic shrub Cneorum pulverulentum, which is native to the Canary Islands. It is a natural product containing a [4.3.1]propellane ring system as the northern part of the molecule and a 5,5-spiroketal unit and a butenolide moiety as the southern part. Despite the intriguing structure, the molecule has not attracted synthetic attention except from our group. The northern DEFG ring system of cneorin C is an ideal candidate for the copper-catalyzed intramolecular cyclopropanation of a diazomalonate. The synthesis of the DEFG ring system of cneorin C is described. The key steps include: 1) an enzymatic kinetic resolution providing the first stereogenic center of the molecule in an enantioselective fashion, 2) intramolecular cyclopropanation of a diazomalonate providing the EFG ring fragment and 3) an anionic cyclization of a sulfone yielding the [4.3.1]propellane ring system. en
dc.format.extent 131
dc.format.mimetype application/pdf
dc.language.iso en en
dc.publisher Helsinki University of Technology en
dc.publisher Teknillinen korkeakoulu fi
dc.relation.ispartofseries Helsinki University of Technology, Organic chemistry report en
dc.relation.ispartofseries 1/2005 en
dc.subject.other Chemistry en
dc.title Cneorins, cyclopropanes and propellanes : synthesis of windmill molecules en
dc.type G4 Monografiaväitöskirja fi
dc.description.version reviewed en
dc.contributor.department Department of Chemical Technology en
dc.contributor.department Kemian tekniikan osasto fi
dc.subject.keyword total synthesis en
dc.subject.keyword natural products en
dc.subject.keyword cneorin C en
dc.subject.keyword propellanes en
dc.subject.keyword intramolecular cyclopropanation en
dc.identifier.urn urn:nbn:fi:tkk-005230
dc.type.dcmitype text en
dc.type.ontasot Väitöskirja (monografia) fi
dc.type.ontasot Doctoral dissertation (monograph) en
dc.contributor.lab Laboratory of Organic Chemistry en
dc.contributor.lab Orgaanisen kemian laboratorio fi


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