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

Nature Communications
Lian-Dong GuoJing Xu

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.

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Citations

Sep 22, 2020·Chemistry : a European Journal·Huilin LiXuegong She
Aug 6, 2021·Chemical Society Reviews·Matthew S GalliherCorey R J Stephenson
Aug 20, 2020·Journal of the American Chemical Society·Guangpeng XuChao Li
Oct 20, 2020·Accounts of Chemical Research·Lian-Dong GuoJing Xu
Oct 26, 2021·Chemical Communications : Chem Comm·Subhamoy BiswasAnil K Saikia

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Methods Mentioned

BETA
X-ray
column chromatography
NMR

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