Lipase-mediated resolution of the hydroxy-cyclogeraniol isomers: application to the synthesis of the enantiomers of karahana lactone, karahana ether, crocusatin C and gamma-cyclogeraniol (Articolo in rivista)

Type

• Articolo in rivista (Classe)
• Prodotto della ricerca (Classe)

Label

• Lipase-mediated resolution of the hydroxy-cyclogeraniol isomers: application to the synthesis of the enantiomers of karahana lactone, karahana ether, crocusatin C and gamma-cyclogeraniol (Articolo in rivista) (literal)

Anno

• 2009-01-01T00:00:00+01:00 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi

• 10.1016/j.tetasy.2009.05.013 (literal)

Alternative label

• Serra S., Gatti F.G., Fuganti C. (2009)
  Lipase-mediated resolution of the hydroxy-cyclogeraniol isomers: application to the synthesis of the enantiomers of karahana lactone, karahana ether, crocusatin C and gamma-cyclogeraniol
  in Tetrahedron: asymmetry (Print)
  (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

• Serra S., Gatti F.G., Fuganti C. (literal)

Pagina inizio

• 1319 (literal)

Pagina fine

• 1329 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

• 20 (literal)

Rivista

• Tetrahedron: asymmetry (Rivista)

Note

• ISI Web of Science (WOS) (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

• CNR, Istituto di Chimica del Riconoscimento Molecolare, I-20131 Milano, Italy Politecnico di Milano, Dipartimento di Chimica, Ingegneria Chimica & Materiali, I-20131 Milano, Italy (literal)

Titolo

• Lipase-mediated resolution of the hydroxy-cyclogeraniol isomers: application to the synthesis of the enantiomers of karahana lactone, karahana ether, crocusatin C and gamma-cyclogeraniol (literal)

Abstract

• A comprehensive study on the lipase PS-mediated resolution of different hydroxy-geraniol isomers is reported. A number of alpha-, beta- and gamma-isomers hearing a 2-, 3- or 4-hydroxy functional group were synthesised regioselectively and then Submitted to the lipase-mediated kinetic acetylation. The latter experiments showed that the 2-hydroxy isomers 4, 5 and 14 (alpha, gamma and beta, respectively) as well as cis-3-hydroxy alpha-cyclogeraniol 7 and cis-4-hydroxy gamma-cyclogeraniol 10 could be easily resolved by this procedure, The enantiomeric purity of the main part of these compounds was increased by recrystallisation and the enantiopure diols obtained were used as building blocks for the synthesis of the natural terpenoids karahana lactone, karahana ether and crocusatin C and for the preparation of the synthetic intermediate gamma-cyclogeraniol. The absolute configurations of the enantiomers of the diols 7, 10, 14 and 19 were determined by chemical correlation with the known compounds 40, 41, 39 and 41, respectively. (literal)

Prodotto di

• Applicazioni sintetiche della biocatalisi (PM.P03.009.002) (Modulo)
• Istituto di chimica del riconoscimento molecolare (ICRM) (Istituto)

Autore CNR

• STEFANO SERRA (Unità di personale interno)
• CLAUDIO FUGANTI (Persona)

Incoming links:

Autore CNR di

• STEFANO SERRA (Unità di personale interno)
• CLAUDIO FUGANTI (Persona)

Prodotto

• Istituto di chimica del riconoscimento molecolare (ICRM) (Istituto)
• Applicazioni sintetiche della biocatalisi (PM.P03.009.002) (Modulo)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi

• Tetrahedron: asymmetry (Rivista)