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.
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.
Karche
Navnath P
NP
Department of Chemistry, Garware Research Centre, University of Pune, India.
Jachak
Santosh M
SM
Dhavale
Dilip D
DD
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
D001391:Azo Compounds; C046499:griseolic acid; D012238:Rhodium; D005947:Glucose; D000241:Adenosine