New Access to Indolizidine and Pyrrolizidine Alkaloids from an Enantiopure Proline:  Total Syntheses of (−)-Lentiginosine and (1R,2R,7aR)-Dihydroxypyrrolizidine

• Published in: Journal of organic chemistry Vol. 72; no. 15; pp. 5592 - 5597
• Main Authors: Angle, Steven R, Bensa, David, Belanger, Dominique S
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 20.07.2007; Amer Chemical Soc
• Subjects: Alkaloids - chemistry; Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Organic chemistry; Physical Sciences; Preparations and properties; Proline - chemistry; Pyrrolizidine Alkaloids - chemical synthesis; Pyrrolizidine Alkaloids - chemistry; Science & Technology; Spectrometry, Mass, Fast Atom Bombardment; Stereoisomerism; REARRANGEMENT; CYCLOADDITION; NATURAL LENTIGINOSINE; PIPERIDINE; ASYMMETRIC SYNTHESES; POLYHYDROXYLATED PYRROLIZIDINES; STEREOSELECTIVE-SYNTHESIS; INHIBITORS; DERIVATIVES; CYCLIZATION; Nitrogen heterocycle; Proline; Total synthesis; Ester; α-Aminoacid; Alkaloid; Alditol; Pyrrolizidine derivatives; Benzylic compound; Aminoacid; Indolizidine derivative; Mannitol; Chemical synthesis
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo070462w

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.