A stereoselective approach to indolizidine and pyrrolizidine alkaloids: total synthesis of (-)-lentiginosine, (-)-epi-lentiginosine and (-)-dihydroxypyrrolizidine.
A simple and highly efficient approach to hydroxylated pyrrolizidine and indolizidine is developed from an aldehyde as a starting material using organocatalytic and asymmetric dihydroxylation reactions as key steps. Its application to the total synthesis of (-)-lentiginosine, (-)-epi-1,2-lentiginosine and (-)-dihydroxypyrrolizidine is also reported.
Division of Organic Chemistry, CSIR-NCL (National Chemical Laboratory), Pune 411008, India. pk.tripathi@ncl.res.in.
Shruti Vandana
SV
Kauloorkar
Vishwajeet
V
Jha
Ganesh
G
Jogdand
Pradeep
P
Kumar
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D006900:Hydroxylation; D054836:Indolizidines / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D054836:Indolizidines; D011763:Pyrrolizidine Alkaloids; C063984:lentiginosine