Densely functionalized chiral pyrroles from endocyclic, exocyclic, and acyclic vinyl sulfone-modified carbohydrates.
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.
Bhattacharya
Rahul
R
Department of Chemistry, Indian Institute of Technology, Kharagpur 721 302, India.
Atta
Ananta Kumar
AK
Dey
Debanjana
D
Pathak
Tanmaya
T
D002241:Carbohydrates / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D013237:Stereoisomerism; D013450:Sulfones / Q000138:chemical synthesis / Q000737:chemistry*
D002241:Carbohydrates; D011758:Pyrroles; D013450:Sulfones; C009873:divinyl sulfone