Total Syntheses of Daphnezomine L-type and Secodaphniphylline-type Daphniphyllum Alkaloids via Late-Stage C-N Bond Activation

Hu，Jingping1,2; Guo，Lian Dong2; Chen，Wenqing2; Jiang，Yuyang2; Pu，Fan2; Ning，Chengqing2,4; Xu，Jing2,3

2022

10.1021/acs.orglett.2c02988

ORGANIC LETTERS   Impact Factor & Quartile

1523-7060

1523-7052

Here, we report the first total syntheses of daphnezomine L-type alkaloids daphnezomine L methyl ester and calyciphylline K via late-stage C-N bond activation. The first synthesis of secodaphniphylline-type alkaloid caldaphnidine D was also achieved via a similar strategy. Other key transformations employed in our synthesis were a facile vicinal diol olefination and an efficient radical cyclization cascade. Biological studies indicated two synthetic compounds possess promising neuroprotective activity.

English

NI Journal Papers

Corresponding

CHEMISTRY

2-s2.0-85139431563

Scopus

1.School of Chemistry and Chemical Engineering,Harbin Institute of Technology,Harbin,150001,China
2.Department of Chemistry,Shenzhen Grubbs Institute,Guangdong Provincial Key Laboratory of Catalysis,Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis,Southern University of Science and Technology,Shenzhen,518055,China
3.Shenzhen Bay Laboratory,Shenzhen,518132,China
4.SUSTech Academy for Advanced Interdisciplinary Studies,Shenzhen,Guangdong,518055,China

Hu，Jingping,Guo，Lian Dong,Chen，Wenqing,et al. Total Syntheses of Daphnezomine L-type and Secodaphniphylline-type Daphniphyllum Alkaloids via Late-Stage C-N Bond Activation[J]. ORGANIC LETTERS,2022.

Hu，Jingping.,Guo，Lian Dong.,Chen，Wenqing.,Jiang，Yuyang.,Pu，Fan.,...&Xu，Jing.(2022).Total Syntheses of Daphnezomine L-type and Secodaphniphylline-type Daphniphyllum Alkaloids via Late-Stage C-N Bond Activation.ORGANIC LETTERS.

Hu，Jingping,et al."Total Syntheses of Daphnezomine L-type and Secodaphniphylline-type Daphniphyllum Alkaloids via Late-Stage C-N Bond Activation".ORGANIC LETTERS (2022).