Asymmetric total synthesis of yuzurimine-type Daphniphyllum alkaloid (+)-caldaphnidine J

Lian-Dong Guo, Yan Zhang, Jingping Hu, Chengqing Ning, Heyifei Fu, Yuye Chen and Jing Xu ()
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Lian-Dong Guo: Southern University of Science and Technology
Yan Zhang: Southern University of Science and Technology
Jingping Hu: Southern University of Science and Technology
Chengqing Ning: Southern University of Science and Technology
Heyifei Fu: Southern University of Science and Technology
Yuye Chen: Southern University of Science and Technology
Jing Xu: Southern University of Science and Technology

Nature Communications, 2020, vol. 11, issue 1, 1-6

Abstract: Abstract Ever since Hirata’s report of yuzurimine in 1966, nearly fifty yuzurimine-type alkaloids have been isolated, which formed the largest subfamily of the Daphniphyllum alkaloids. Despite extensive synthetic studies towards this synthetically challenging and biologically intriguing family, no total synthesis of any yuzurimine-type alkaloids has been achieved to date. Here, the first enantioselective total synthesis of (+)-caldaphnidine J, a highly complex yuzurimine-type Daphniphyllum alkaloid, is described. Key transformations of this approach include a highly regioselective Pd-catalyzed hydroformylation, a samarium(II)-mediated pinacol coupling, and a one-pot Swern oxidation/ketene dithioacetal Prins reaction. Our approach paves the way for the synthesis of other yuzurimine-type alkaloids and related natural products.

Date: 2020
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DOI: 10.1038/s41467-020-17350-x

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