Liao Xuebin, Huang Shengming, Zhou Hao, Parrish Damon, Cook James M
Department of Chemistry and Biochemistry, University of Wisconsin-Milwaukee, 3210 North Cramer Street, Milwaukee, Wisconsin 53211, USA.
Org Lett. 2007 Apr 12;9(8):1469-71. doi: 10.1021/ol070148o. Epub 2007 Mar 15.
[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.