Total Synthesis of Yuzurine-type Alkaloid Daphgraciline

Li，Li Xuan1,2; Min，Long1; Yao，Tian Bing1; Ji，Shu Xiao1; Qiao，Chuang1; Tian，Pei Lin1; Sun，Jianwei2; Li，Chuang Chuang1,3

2022

10.1021/jacs.2c09548

Journal of the American Chemical Society   Impact Factor & Quartile

0002-7863

1520-5126

The first total synthesis of daphgraciline has been achieved, which also represents the first example of the synthesis of Daphniphyllum yuzurine-type alkaloids (∼50 members). The unique bridged azabicyclo[4.3.1] ring system in the yuzurine-type subfamily was efficiently and diastereoselectively assembled via a mild type II [5+2] cycloaddition for the first time. The compact tetracyclic [6-7-5-5] skeleton was installed efficiently via an intramolecular Diels-Alder reaction, followed by a benzilic acid-type rearrangement. The synthetically challenging spiro tetrahydropyran moiety in the final product was installed diastereoselectively via a TiIII-mediated reductive epoxide coupling reaction. Potential access to enantioenriched daphgraciline is presented.

English

NI Journal Papers

First

2-s2.0-85139529810

Scopus

1.Shenzhen Grubbs Institute,Department of Chemistry,Guangdong Provincial Key Laboratory of Catalytic Chemistry,Southern University of Science and Technology,Shenzhen,518055,China
2.Department of Chemistry,The Hong Kong University of Science and Technology,Kowloon,Clear Water Bay,Hong Kong
3.Shenzhen Bay Laboratory,Shenzhen,518132,China

Li，Li Xuan,Min，Long,Yao，Tian Bing,et al. Total Synthesis of Yuzurine-type Alkaloid Daphgraciline[J]. Journal of the American Chemical Society,2022.

Li，Li Xuan.,Min，Long.,Yao，Tian Bing.,Ji，Shu Xiao.,Qiao，Chuang.,...&Li，Chuang Chuang.(2022).Total Synthesis of Yuzurine-type Alkaloid Daphgraciline.Journal of the American Chemical Society.

Li，Li Xuan,et al."Total Synthesis of Yuzurine-type Alkaloid Daphgraciline".Journal of the American Chemical Society (2022).