title: Synthesis of griseolic acid analogues: regioselective alpha-facial [1,2]-migration in the rhodium acetate catalyzed reaction of D-glucose derived alpha-diazo-beta-keto ester.
abstract: This paper describes an efficient route for the synthesis of known and novel griseolic acid analogues 1d and 1e, respectively. The key intermediate dioxabicyclo derivative 6, with the required stereochemical orientation at C6, was obtained by rhodium acetate catalyzed reaction of d-glucose derived alpha-diazo-beta-keto ester 5 in a novel high-yielding methodology.
authors.affiliation: Department of Chemistry, Garware Research Centre, University of Pune, India.
authors.forename: Navnath P
authors.initials: NP
authors.lastname: Karche
authors.forename: Santosh M
authors.initials: SM
authors.lastname: Jachak
authors.forename: Dilip D
authors.initials: DD
authors.lastname: Dhavale
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D005947:Glucose / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
chemical_list: D001391:Azo Compounds; C046499:griseolic acid; D012238:Rhodium; D005947:Glucose; D000241:Adenosine