Synthesis of pentahydroxy indolizidine alkaloids using ring closing metathesis: attempts to find the correct structure of uniflorine A.
Ring closing metathesis of d-glucose derived diene-substrate containing nitrogen functionality followed by asymmetric dihydroxylation afforded sugar substituted dihydroxylated pyrrolidines 8a-c which on 1,2-acetonide deprotection and reductive amination afforded putative uniflorine A 2a and its analogues 2b-c, respectively.
Karanjule
Narayan S
NS
Garware Research Centre, Department of Chemistry, University of Pune, Pune-411 007, India.
Markad
Shankar D
SD
Dhavale
Dilip D
DD
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D006900:Hydroxylation; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D000470:Alkaloids; D007212:Indolizines; C487671:uniflorine A