Enzyme-mediated preparation of enantioenriched forms of trans- and cis-p-menthan-1,8-dien-5-ol (Articolo in rivista)

Type
Label
  • Enzyme-mediated preparation of enantioenriched forms of trans- and cis-p-menthan-1,8-dien-5-ol (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.2006.02.012 (literal)
Alternative label
  • Brenna E., Fuganti C., Gatti F.G., Perero M., Serra S. (2006)
    Enzyme-mediated preparation of enantioenriched forms of trans- and cis-p-menthan-1,8-dien-5-ol
    in Tetrahedron: asymmetry (Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Brenna E., Fuganti C., Gatti F.G., Perero M., Serra S. (literal)
Pagina inizio
  • 792 (literal)
Pagina fine
  • 796 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 17 (literal)
Rivista
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • CNR-ICRM Politecnico di Milano (literal)
Titolo
  • Enzyme-mediated preparation of enantioenriched forms of trans- and cis-p-menthan-1,8-dien-5-ol (literal)
Abstract
  • The synthesis of the trans-p-menthan-5-ol (+/-)-1 was carried out by Diels-Alder cycloaddition of 3-keto-1-butenyl-acetate 3 with isoprene followed by Wittig methylenation. PS lipase resolution of the alcohol afforded acetate (-)-5 with 98% ec, which was hydrolysed to give (-)1. Alternatively, enzymatic hydrolysis of a keto ester followed by Wittig methylenation and hydrolysis afforded the same alcohol with an ee of 86%. The cis-p-menthan-5-ol (-)-2 was obtained by Swern oxidation of (-)-1. followed by diastereoselective reduction with L-Selectride without lost of enantiomeric excess. (literal)
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