title: Total synthesis of (+)-lactacystin.
abstract: A double stereodifferentiating crotylation between aldehyde 1 and silane (S)-2 to afford homoallylic alcohol 3 is the key diastereoselective step (anti:syn >30:1) in an efficient asymmetric synthesis of (+)-lactacystin. This compound is a metabolite isolated from Streptomyces sp. OM-6519 that exhibits significant neurotrophic activity. An additional important step in the synthesis is a catalytic asymmetric aminohydroxylation used as the key step in the synthesis of the (2R,3S)-hydroxyleucine synthon.
authors.affiliation: Department of Chemistry, Metcalf Center for Science and Engineering, Boston University, Boston, MA 02215, USA, Fax: (+1) 617-353-6466. panek@chem.bu.edu.
authors.forename: J S
authors.initials: JS
authors.lastname: Panek
authors.forename: C E
authors.initials: CE
authors.lastname: Masse
keywords: Asymmetric synthesis; Enzyme inhibitors; Lactacystin; Lactones; Total synthesis