An interrupted Fischer indolization approach toward fused indoline-containing natural products.
An efficient method to access the fused indoline ring system present in a multitude of bioactive molecules has been developed. The strategy involves the condensation of hydrazines with latent aldehydes to ultimately deliver indoline-containing products by way of an interrupted Fischer indolization sequence. Our studies show that the approach will likely be amenable to the synthesis of complex targets, such as the communesin natural products.
Boal
Ben W
BW
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
Schammel
Alex W
AW
Garg
Neil K
NK
D000447:Aldehydes / Q000737:chemistry*; D001688:Biological Products / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D006834:Hydrazines / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D010830:Physostigmine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D000447:Aldehydes; D001688:Biological Products; D006576:Heterocyclic Compounds, 4 or More Rings; D006834:Hydrazines; D007211:Indoles; C092643:physovenine; C057812:indoline; D010830:Physostigmine