Asymmetric synthesis of synthetic alkaloids by a tandem biocatalysis/Ugi/Pictet-Spengler-type cyclization sequence.
We have combined the biocatalytic desymmetrization of 3,4-cis-substituted meso-pyrrolidines with an Ugi-type multicomponent reaction followed in situ by a Pictet-Spengler-type cyclization reaction sequence for the rapid asymmetric synthesis of alkaloid-like polycyclic compounds.
Znabet
Anass
A
Department of Chemistry & Pharmaceutical Sciences, Vrije Universiteit Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands.
Zonneveld
Job
J
Janssen
Elwin
E
De Kanter
Frans J J
FJ
Helliwell
Madeleine
M
Turner
Nicholas J
NJ
Ruijter
Eelco
E
Orru
Romano V A
RV
D000470:Alkaloids / Q000096:biosynthesis* / Q000737:chemistry*; D001234:Aspergillus niger / Q000201:enzymology; D055162:Biocatalysis; D003500:Cyclization; D008995:Monoamine Oxidase / Q000378:metabolism; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013379:Substrate Specificity
D000470:Alkaloids; D008995:Monoamine Oxidase