title: Divergent cycloaddition and ring-closing metathesis approaches to indolizidine and pyrrolo[1,2-a]azepine skeletons from a chiral precursor: an expeditious route to (-)-8-epi-swainsonine triacetate.
abstract: [reaction: see text] A divergent strategy for the synthesis of diverse azabicyclic ring systems has been developed in which a chiral N-allylpyrrolidine derivative, obtained from a carbohydrate precursor was converted to (-)-8-epi-swainsonine triacetate by RCM and to a pyrrolo[1,2-a]azepine derivative and a 3-hydroxymethyl-substituted indolizidine by N-allylcarbohydrate nitrone and nitrile oxide cycloadditions.
authors.affiliation: Indian Institute of Chemical Biology, Kolkata.
authors.forename: Madhumita
authors.initials: M
authors.lastname: Nath
authors.forename: Ranjan
authors.initials: R
authors.lastname: Mukhopadhyay
authors.forename: Anup
authors.initials: A
authors.lastname: Bhattacharjya
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D007212:Indolizines / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry; D017026:Swainsonine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C414028:1,2-di-epi-swainsonine; D000470:Alkaloids; D007212:Indolizines; D011758:Pyrroles; D017026:Swainsonine