title: Enantioselective synthesis of natural trinorsesquiterpene tetralones by chemo-enzymatic approaches.
abstract: The enantioselective syntheses of both the enantiomeric forms of the four natural tetralones 1a-d are here described. The aforementioned trinorsesquiterpenes were prepared starting either from substituted (S)-3-arylbutanols 5a-c or from substituted (S)-2-arylpropanols 7a-c. The latter chiral building blocks were in turn obtained through two different kinds of enzymatic transformations consisting of the baker's yeast mediated reduction of substituted (E)-3-aryl-but-2-enals 4a-c and the lipase-mediated resolution of racemic 2-arylpropanols 7a-c, respectively. Further key steps of the presented syntheses were C1 and C2 homologation procedures as well as the ring closure of the substituted 4-aryl-pentanoic acids 3a-c. By these means the target compounds were obtained in good yields and with very high stereoisomeric purity. In addition, the trinorsesquiterpene schiffnerone-B was synthesized for the first time and its absolute configuration was unambiguously assigned.
authors: C.N.R., Istituto di Chimica del Riconoscimento Molecolare, Via Mancinelli, 7 I-20131 Milano, Italy. stefano.serra@cnr.it
authors: Stefano
authors: S
authors: Serra
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis; D008049:Lipase / Q000378:metabolism; D010084:Oxidation-Reduction; D012441:Saccharomyces cerevisiae / Q000378:metabolism; D013237:Stereoisomerism; D044024:Tetralones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001688:Biological Products; D044024:Tetralones; D008049:Lipase