title: Chemoenzymatic synthesis and synthetic application of enantiopure aminocyclopentenols: total synthesis of carbocyclic (+)-uracil polyoxin C and its alpha-epimer.
abstract: Carbocyclic uracil polyoxin C (+)-2 and its alpha-epimer (-)-3 were synthesized in an efficient fashion from cis-4-(N-tert-butylcarbamoyl)cyclopent-2-en-1-ol (+/-)-7. The synthesis incorporates a concise, inexpensive chemoenzymatic synthesis of enantiopure aminocyclopentenols, a Pd(0)-catalyzed substitution reaction, and a mild reduction of an alpha-nitro ester by TiCl(3)/sodium borohydride. Significantly, this process demonstrates the synthetic utility of the versatile enantiopure aminocyclopentenol building block (-)-4.
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
authors.forename: Fangzheng
authors.initials: F
authors.lastname: Li
authors.forename: John B
authors.initials: JB
authors.lastname: Brogan
authors.forename: Jennifer L
authors.initials: JL
authors.lastname: Gage
authors.forename: Deyi
authors.initials: D
authors.lastname: Zhang
authors.forename: Marvin J
authors.initials: MJ
authors.lastname: Miller
mesh_terms: D008968:Molecular Conformation; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014498:Uracil / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
chemical_list: D011741:Pyrimidine Nucleosides; C414026:uracil polyoxin C; D014498:Uracil