title: Synthesis of indolizidines from optically pure α-amino acids via stereocontrolled rhodium-catalyzed hydroformylation of N-allylpyrroles.
abstract: Indolizidine alkaloids have attracted considerable attention because of their vast array of structural diversity and varied biological activity. This article relates the results that we obtained in the field of the total synthesis of indolizidines from α-amino acids, based on the rhodium-catalyzed hydroformylation of N-allylpyrroles intermediates. The formed pyrrolylbutanals undergo an intramolecular cyclodehydration to 5,6-dihydroindolizines, which are fully hydrogenated to indolizidines. All reaction sequences are stereocontrolled: indeed, the chiral center in the starting amino acid is transferred into 5,6-dihydroindolizine moiety with complete stereochemical integrity and the new stereogenic center at C9 carbon atom in the final indolizidines is generated in only one configuration.
authors.affiliation: Dipartimento di Chimica e Chimica Industriale, Università di Pisa, via Risorgimento 35, 56126 Pisa, Italy. lazza@dcci.unipi.it
authors.forename: Raffaello
authors.initials: R
authors.lastname: Lazzaroni
authors.forename: Roberta
authors.initials: R
authors.lastname: Settambolo
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006865:Hydrogenation; D054836:Indolizidines / Q000138:chemical synthesis* / Q000737:chemistry*; D007212:Indolizines / Q000138:chemical synthesis / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C413205:167B indolizidine; D000596:Amino Acids; D054836:Indolizidines; D007212:Indolizines; D012238:Rhodium