Synthesis of the enantiomeric forms of alpha- and gamma-damascone starting from commercial racemic alpha-ionone (Articolo in rivista)

Type

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

Label

• Synthesis of the enantiomeric forms of alpha- and gamma-damascone starting from commercial racemic alpha-ionone (Articolo in rivista) (literal)

Anno

• 2006-01-01T00:00:00+01:00 (literal)

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

• 10.1016/j.tetasy.2006.05.024 (literal)

Alternative label

• Serra S., Fuganti C. (2006)
  Synthesis of the enantiomeric forms of alpha- and gamma-damascone starting from commercial racemic alpha-ionone
  in Tetrahedron: asymmetry (Print)
  (literal)

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

• Serra S., Fuganti C. (literal)

Pagina inizio

• 1573 (literal)

Pagina fine

• 1580 (literal)

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

• 17 (literal)

Rivista

• Tetrahedron: asymmetry (Rivista)

Note

• ISI Web of Science (WOS) (literal)

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

• CNR-ICRM Politecnico di Milano (literal)

Titolo

• Synthesis of the enantiomeric forms of alpha- and gamma-damascone starting from commercial racemic alpha-ionone (literal)

Abstract

• A straightforward synthesis of both enantiomers of alpha- and gamma-damascone is described. The title compounds were prepared by a divergent pathway starting from the enantiomeric forms of (6RS,7SR,9RS)-7-hydroxy-7,8-dihydro-alpha-ionol and of (6RS,7SR,9RS)-7hydroxy-7.8-dihydro-gamma-ionol. These building blocks were obtained from racemic alpha-ionone in four and five steps, respectively. The 7-hydroxy group was introduced by regio- and diastereoselective epoxidation of the conjugated double bond followed by reductive opening of the oxirane ring. The hydroxy-ketone obtained was reduced diastereo selectively to trans-alpha-diol that could be converted to the trans-gamma-diol by photochemical isomerization. Both diols were then resolved by lipase-mediated acetylation. (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)
• 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)