Biogenetically inspired enantioselective approach to Indolo[2,3-a]- and benzo[a]quinolizidine alkaloids from a synthetic equivalent of secologanin.
[reaction: see text] Racemic oxodiester 1 undergoes stereoselective cyclocondensation with (S)-tryptophanol, (S)-(3,4-dimethoxyphenyl)alaninol, or the corresponding amino acids, in a process involving a tandem dynamic kinetic resolution/desymmetrization of diastereotopic groups, to give bicyclic lactams, which are cyclized to substituted indolo[2,3-a]- and benzo[a]quinolizidines.
Bassas
Oriol
O
Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Spain.
Llor
Núria
N
Santos
Maria M M
MM
Griera
Rosa
R
Molins
Elies
E
Amat
Mercedes
M
Bosch
Joan
J
D000596:Amino Acids / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D057888:Iridoid Glucosides; D039823:Iridoids / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis; D015394:Molecular Structure; D011807:Quinolizines / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D001688:Biological Products; D026121:Indole Alkaloids; D057888:Iridoid Glucosides; D039823:Iridoids; D007769:Lactams; D011807:Quinolizines; C021086:secologanin