Asymmetric cinnamylation of N-tert-butanesulfinyl imines with cinnamyl acetates: total syntheses of (+)-lycoricidine and (+)-7-deoxypancratistatin

Sen-Lin Cai; Bin-Hua Yuan; Yi-Xiang Jiang; Guo-Qiang Lin; Xing-Wen Sun

doi:10.1039/c7cc00108h

Asymmetric cinnamylation of N-tert-butanesulfinyl imines with cinnamyl acetates: total syntheses of (+)-lycoricidine and (+)-7-deoxypancratistatin

Chem Commun (Camb). 2017 Mar 23;53(25):3520-3523. doi: 10.1039/c7cc00108h.

Authors

Sen-Lin Cai¹, Bin-Hua Yuan¹, Yi-Xiang Jiang¹, Guo-Qiang Lin¹, Xing-Wen Sun¹

Affiliation

¹ Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China. sunxingwen@fudan.edu.cn.

PMID: 28243660
DOI: 10.1039/c7cc00108h

Abstract

Highly diastereoselective palladium catalyzed cinnamylation of N-tert-butanesulfinyl imines with cinnamyl acetates has been established to provide enantioenriched β-aryl homoallylic amines. The synthetic application of this stragety has been successfully demonstrated in the concise total syntheses of antitumor natural products (+)-lycoricidine and (+)-7-deoxypancratistatin.