Cascade approach toward the core structure of neosarpagine.
[reaction: see text] A palladium-catalyzed domino sequence was developed to rapidly construct the core structure of neosarpagine and other quinuclidine-related alkaloids. The cyclization of ketone 11 to ethylidene 4 with Pd(dba)2, DPEphos, LiHMDS, and ZnCl2 in THF represents a new domino process wherein a nonstabilized enolate served as a nucleophile.
Liao
Xuebin
X
Department of Chemistry and Biochemistry, University of Wisconsin-Milwaukee, 3210 North Cramer Street, Milwaukee, Wisconsin 53211, USA.
Huang
Shengming
S
Zhou
Hao
H
Parrish
Damon
D
Cook
James M
JM
D002384:Catalysis; D026121:Indole Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D000078183:Oxindoles; D010165:Palladium / Q000737:chemistry; D011812:Quinuclidines / Q000737:chemistry
D026121:Indole Alkaloids; D007659:Ketones; D000078183:Oxindoles; D011812:Quinuclidines; C512190:macroline; D010165:Palladium; C475809:sarpagine