New access to indolizidine and pyrrolizidine alkaloids from an enantiopure proline: total syntheses of (-)-lentiginosine and (1R,2R,7aR)-dihydroxypyrrolizidine.
A new approach to the synthesis of indolizidine and pyrrolizidine skeletons is reported. (-)-Lentiginosine and (1R,2R,7aR)-dihydroxypyrrolizidine have both been synthesized in 13 steps from di-O-isopropylidene-d-mannitol. The common key intermediate is (-)-dihydroxyproline benzyl ester 10.
Angle
Steven R
SR
Department of Chemistry, University of California, Riverside, CA 92521-0403, USA. steven.angle@wright.edu
Bensa
David
D
Belanger
Dominique S
DS
D000470:Alkaloids / Q000737:chemistry*; D011392:Proline / Q000737:chemistry*; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism
D000470:Alkaloids; D011763:Pyrrolizidine Alkaloids; C063984:lentiginosine; D011392:Proline