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Total synthesis of (+)-lactacystin
1Department of Chemistry, Metcalf Center for Science and Engineering, Boston University, Boston, MA 02215, USA, Fax: (+1) 617-353-6466. panek@chem.bu.edu.
Angewandte Chemie (International Ed. in English)
|August 21, 2014
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.