Total synthesis of (+/-)-strychnine via a [4 + 2]-cycloaddition/rearrangement cascade.
A new strategy for the synthesis of the Strychnos alkaloid (+/-)-strychnine has been developed and is based on an intramolecular [4 + 2]-cycloaddition/rearrangement cascade of an indolyl-substituted amidofuran. The critical D-ring was assembled by an intramolecular palladium-catalyzed enolate-driven cross-coupling of an N-tethered vinyl iodide. [reaction: see text].
Zhang
Hongjun
H
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
Boonsombat
Jutatip
J
Padwa
Albert
A
D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000737:chemistry*; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D013331:Strychnine / Q000138:chemical synthesis* / Q000737:chemistry; D014753:Vinyl Compounds / Q000737:chemistry
D005663:Furans; D006847:Hydrocarbons, Iodinated; D009942:Organometallic Compounds; D014753:Vinyl Compounds; D010165:Palladium; D013331:Strychnine