title: Enzymatic kinetic resolution of internal propargylic diols. Part I: a new approach for the synthesis of (S)-pent-2-yn-1,4-diol, a natural product from Clitocybe catinus.
abstract: Internal bis-substituted propargylic diols were subjected to enzymatic kinetic resolution promoted by CAL-B. Employing a two round sequence EKR, mono- and bis-acetoxy propargylic products were obtained in a high enantiomeric ratio (E > 200). The efficiently resolved chiral 8b was applied in a concise synthesis of (S)-1b, an optically active natural product produced by fungi Clitocybe catinus.
authors.affiliation: Departamento de Química Fundamental, Universidade Federal de Pernambuco - UFPE, Av. Jornalista Aníbal Fernandes S/N, Cidade Universitária, CEP: 50740-560, Recife, PE, Brasil. princivalj@yahoo.com.br.
authors.forename: Jeiely G
authors.initials: JG
authors.lastname: Ferreira
authors.forename: Cleverson R
authors.initials: CR
authors.lastname: Princival
authors.forename: Dyego M
authors.initials: DM
authors.lastname: Oliveira
authors.forename: Renata X
authors.initials: RX
authors.lastname: Nascimento
authors.forename: Jefferson L
authors.initials: JL
authors.lastname: Princival
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D001487:Basidiomycota / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D005656:Fungal Proteins / Q000737:chemistry / Q000378:metabolism; D007700:Kinetics; D008049:Lipase / Q000737:chemistry / Q000378:metabolism; D000439:Pentanols / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D001688:Biological Products; D005656:Fungal Proteins; D000439:Pentanols; C000605887:pent-2-yn-1,4-diol; D008049:Lipase; C431349:lipase B, Candida antarctica