title: Synthesis of L-altro-1-deoxynojirimycin, D-allo-1-deoxynojirimycin, and D-galacto-1-deoxynojirimycin from a single chiral cyanohydrin.
abstract: The chemoenzymatic synthesis of three 1-deoxynojirimycin-type iminosugars is reported. Key steps in the synthetic scheme include a Dibal reduction-transimination-sodium borohydride reduction cascade of reactions on an enantiomerically pure cyanohydrin, itself prepared employing almond hydroxynitrile lyase (paHNL) as the common precursor. Ensuing ring-closing metathesis and Upjohn dihydroxylation afford the target compounds.
authors.affiliation: Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
authors.forename: Adrianus M C H
authors.initials: AM
authors.lastname: van den Nieuwendijk
authors.forename: Mark
authors.initials: M
authors.lastname: Ruben
authors.forename: Sander E
authors.initials: SE
authors.lastname: Engelsma
authors.forename: Martijn D P
authors.initials: MD
authors.lastname: Risseeuw
authors.forename: Richard J B H N
authors.initials: RJ
authors.lastname: van den Berg
authors.forename: Rolf G
authors.initials: RG
authors.lastname: Boot
authors.forename: Johannes M
authors.initials: JM
authors.lastname: Aerts
authors.forename: Johannes
authors.initials: J
authors.lastname: Brussee
authors.forename: Gijs A
authors.initials: GA
authors.lastname: van der Marel
authors.forename: Herman S
authors.initials: HS
authors.lastname: Overkleeft
mesh_terms: D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D000446:Aldehyde-Lyases / Q000378:metabolism; D003500:Cyclization; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D027861:Prunus / Q000201:enzymology; D013237:Stereoisomerism
chemical_list: C553780:D-allo-1-deoxynojirimycin; C553779:D-galacto-1-deoxynojirimycin; C553837:L-altro-1-deoxynojirimycin; D009570:Nitriles; C430593:cyanohydrin; D017485:1-Deoxynojirimycin; D000446:Aldehyde-Lyases; C087495:acetone-cyanohydrin lyase