A Short and Efficient Synthesis of Iminosugar 2-Acyl Indolizidine.
A facile and convergent approach has been developed for the stereoselective construction of biologically important polyhydroxylated 2-acyl indolizidine framework using aza-Cope rearrangement-Mannich cyclization as a key step. The generality of this methodology is demonstrated with various lactol-tosylates derived from carbohydrates. The presented method provides an easy access to indolizidine- and tetrahydroindolizine-based iminosugar derivatives in good yields.
Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, India.
Kiran
K
Chinthapally
Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, India.
Reshamina
R
Karthik
Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, India.
Soundararasu
S
Senthilkumar
Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, India.
Sundarababu
S
Baskaran
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D054836:Indolizidines / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D001372:Aza Compounds; D002241:Carbohydrates; D054836:Indolizidines
anticancer agents; aza-Cope-Mannich cyclization; oxazolidine; rearrangement; synthesis design