title: Densely functionalized chiral pyrroles from endocyclic, exocyclic, and acyclic vinyl sulfone-modified carbohydrates.
abstract: A wide range of vinyl sulfone-modified carbohydrates have been prepared as starting materials for the synthesis of polysubstituted chiral pyrroles. All these vinyl sulfones reacted efficiently with ethylisocyanoacetate to generate a plethora of new pyrrole derivatives. Furanosyl rings opened up during pyrrole synthesis, and pyranosyl rings were opened up by reacting the pyrrole with POCl(3)/DMF. This paper also reports one of the most efficient and practical routes for the synthesis of beta-substituted pyrroles.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Kharagpur 721 302, India.
authors.forename: Rahul
authors.initials: R
authors.lastname: Bhattacharya
authors.forename: Ananta Kumar
authors.initials: AK
authors.lastname: Atta
authors.forename: Debanjana
authors.initials: D
authors.lastname: Dey
authors.forename: Tanmaya
authors.initials: T
authors.lastname: Pathak
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D013237:Stereoisomerism; D013450:Sulfones / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D002241:Carbohydrates; D011758:Pyrroles; D013450:Sulfones; C009873:divinyl sulfone