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- W2801129240 abstract "An efficient synthesis of naturally occurring (R)-tylophorine is described. The alkaloid was prepared in seven steps from a known phenanthryl aldehyde with an overall yield of 14.2%. Asymmetric hydrogenation of an allyl alcohol was employed as a key step for installing a stereogenic center with good enantioselectivity (77% ee), and the ee value of the ω-chloro alcohol was improved to 95% by recrystallization. After azidation and oxidation of the enantio-enriched ω-chloro alcohol to the precursor of the Schmidt reaction, the chirality transfer in the stereospecific 1,2-migration furnished the chiral carbon in the alkaloid. Finally, a one-pot deformylation/Pictet-Spengler cyclization completed the total synthesis of (R)-tylophorine." @default.
- W2801129240 created "2018-05-17" @default.
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- W2801129240 date "2018-05-01" @default.
- W2801129240 modified "2023-10-17" @default.
- W2801129240 title "Total synthesis of ( R )-tylophorine by using an asymmetric hydrogenation of the allyl alcohol" @default.
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- W2801129240 doi "https://doi.org/10.1016/j.tetlet.2018.04.052" @default.
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