Rapid access to the Welwitindolinone alkaloid skeleton by cyclization of indolecarboxaldehyde substituted cyclohexanones.
[reaction: see text] A very rapid access to cyclohexanone-bridged indole systems was established by an acid-mediated ring closure of appropriately substituted indole aldehydes, which involved an apparent disproportionation of an aldol-like intermediate. One of the bridged indole intermediates was further transformed into an oxindole having the essential skeleton of the Welwitindolinone alkaloids.
Baudoux
Jérôme
J
School of Chemistry, University of Nottingham, Nottingham, UK.
Blake
Alexander J
AJ
Simpkins
Nigel S
NS
D000447:Aldehydes / Q000737:chemistry*; D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D003500:Cyclization; D003512:Cyclohexanones / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D013997:Time Factors
D000447:Aldehydes; D000470:Alkaloids; D003512:Cyclohexanones; D007211:Indoles; C512179:indolecarboxaldehyde; C036468:cyclohexanone; C030374:indole