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.
[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.
Nath
Madhumita
M
Indian Institute of Chemical Biology, Kolkata.
Mukhopadhyay
Ranjan
R
Bhattacharjya
Anup
A
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
C414028:1,2-di-epi-swainsonine; D000470:Alkaloids; D007212:Indolizines; D011758:Pyrroles; D017026:Swainsonine