Enantioselective Total Synthesis of (-)-Caldaphnidine O via a Radical Cyclization Cascade

Guo, Lian-Dong; Hu, Jingping; Zhang, Yan; Tu, Wentong; Zhang, Yue; Pu, Fan; Xu, Jing1

2019-08-21

10.1021/jacs.9b07558

Journal of the American Chemical Society   影响因子和分区

0002-7863

1520-5126

The synthetically challenging, diverse chemical skeletons and promising biological profiles of the Daphniphyllum alkaloids have generated intense interest from the synthetic chemistry community. Herein, the first and enantioselective total synthesis of (-)-caldaphnidine O, a complex bukittinggine-type Daphniphyllum alkaloid, is described. The key transformations in this concise approach included an intramolecular aza-Michael addition, a ring expansion reaction sequence, a Sm(II)/Fe(III)-mediated Kagan-Molander coupling, and the rapid formation of the entire hexacyclic ring skeleton of the target molecule via a radical cyclization cascade reaction, which was inspired by an unexpected radical detosylation observed in our recent dapholdhamine B synthesis.

SCI ; EI ; IC

英语

NI论文

通讯

SZSTI[JCYJ 20170817110515599] ; SZSTI[KQJSCX20170728154233200]

Chemistry

Chemistry, Multidisciplinary

WOS:000482546400019

AMER CHEMICAL SOC

20193407351195

Addition reactions ; Alkaloids ; Enantioselectivity ; Metabolites ; Molecules ; Musculoskeletal system ; Samarium compounds ; Synthesis (chemical)

Biomechanics, Bionics and Biomimetics:461.3 ; Physical Chemistry:801.4 ; Chemical Reactions:802.2 ; Chemical Products Generally:804 ; Atomic and Molecular Physics:931.3

Web of Science

1.Southern Univ Sci & Technol, Dept Chem, Shenzhen, Peoples R China
2.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen, Peoples R China

Guo, Lian-Dong,Hu, Jingping,Zhang, Yan,et al. Enantioselective Total Synthesis of (-)-Caldaphnidine O via a Radical Cyclization Cascade[J]. Journal of the American Chemical Society,2019,141(33):13043-13048.

Guo, Lian-Dong.,Hu, Jingping.,Zhang, Yan.,Tu, Wentong.,Zhang, Yue.,...&Xu, Jing.(2019).Enantioselective Total Synthesis of (-)-Caldaphnidine O via a Radical Cyclization Cascade.Journal of the American Chemical Society,141(33),13043-13048.

Guo, Lian-Dong,et al."Enantioselective Total Synthesis of (-)-Caldaphnidine O via a Radical Cyclization Cascade".Journal of the American Chemical Society 141.33(2019):13043-13048.