Pd-catalyzed assembly of spirooxindole natural products: a short synthesis of horsfiline.
The Pd-catalyzed intramolecular alpha-arylation of amides is applied to the synthesis of functionalized spirooxindoles. The substrate scope is evaluated, and the reaction is demonstrated to be useful for the assembly of spirooxindole natural products and derivatives thereof. As an application, a new synthesis of horsfiline 1 is presented, giving the natural product in only 4 steps from commercially available amino acid 12.
Deppermann
Nina
N
Dr. Knoell Consult GmbH, Dynamostrasse 19, 68165 Mannheim, Germany.
Thomanek
Heike
H
Prenzel
Alexander H G P
AH
Maison
Wolfgang
W
D001685:Biological Factors / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001685:Biological Factors; D009942:Organometallic Compounds; D013141:Spiro Compounds; C443722:horsfiline; D010165:Palladium