Chemoenzymatic preparation of the p-menth-1,5-dien-9-ol stereoisomers and their use in the enantiospecific synthesis of natural p-menthane monoterpenes (Articolo in rivista)

Type

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

Label

• Chemoenzymatic preparation of the p-menth-1,5-dien-9-ol stereoisomers and their use in the enantiospecific synthesis of natural p-menthane monoterpenes (Articolo in rivista) (literal)

Anno

• 2011-01-01T00:00:00+01:00 (literal)

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

• 10.1016/j.tetasy.2011.07.014 (literal)

Alternative label

• Serra S., Nobile I. (2011)
  Chemoenzymatic preparation of the p-menth-1,5-dien-9-ol stereoisomers and their use in the enantiospecific synthesis of natural p-menthane monoterpenes
  in Tetrahedron: asymmetry (Print)
  (literal)

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

• Serra S., Nobile I. (literal)

Pagina inizio

• 1455 (literal)

Pagina fine

• 1463 (literal)

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

• 22 (literal)

Rivista

• Tetrahedron: asymmetry (Rivista)

Note

• ISI Web of Science (WOS) (literal)

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

• CNR-ICRM Università degli studi di Milano (literal)

Titolo

• Chemoenzymatic preparation of the p-menth-1,5-dien-9-ol stereoisomers and their use in the enantiospecific synthesis of natural p-menthane monoterpenes (literal)

Abstract

• A study on the preparation and synthetic exploitation of the isomeric forms of p-menth-1,5-dien-9-ol is reported. The latter alcohols were prepared in high enantiomeric purity from the easily available enantiomers of carvone. Thus, a chemoenzymatic procedure based on lipase-mediated acetylation, allowed the separation of their diastereoisomeric forms. Moreover, the purity of the chiral building blocks obtained was improved by fractional crystallisation of their 3,5-dinitrobenzoyl derivatives. A number of synthetic applications have also been described. The stereospecific cyclisation of the isomerically pure dienic alcohols gave the isomeric forms of the terpenes dill and epi-dill ether, which were hydrogenated diastereoselectively to the corresponding (1R)- or (1S)-derivatives depending on the catalyst used. The oxidation of the latter ethers turned out to be stereoselective, affording either the corresponding p-menthan-9-oic lactone or the keto-acid derivatives depending on the starting isomer used. (literal)

Prodotto di

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

Autore CNR

• STEFANO SERRA (Unità di personale interno)

Incoming links:

Autore CNR di

• STEFANO SERRA (Unità di personale interno)

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)