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- W2046830939 abstract "The synthesis of (±) -9-demethylprotoemetinol [(±) -3d] was accomplished by LiAlH4 reduction of the tricyclic ester (±) -5 and subsequent debenzylation of the resulting tricyclic alcohol (±) 10. Acetylation of (±) -3d with acetic anhydride and pyridine gave the diacetate (±) -11. The same sequence of reactions starting with (-) -5 afforded (-) -9-demethylprotoernetinol [(-) -3d] and the diacetate (-) -11 through (-) -10. Parallel synthetic routes starting with the isomeric tricyclic esters (±) -9 and (-) -9 produced (±) -and (-) -10-demethylprotoemetinols [(±) -4d and (-) -4d] and the corresponding diacetates [(±) -13 and (-) -13] through (±) -12 and (-) -12, respectively. The correctness of the structure and absolute stereochemistry of an Alangium alkaloid inferred to be 10-demethylprotoemetinol was confirmed by a direct comparison of its diacetate with synthetic (-) -13." @default.
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- W2046830939 date "1987-01-01" @default.
- W2046830939 modified "2023-09-27" @default.
- W2046830939 title "Quinolizidines. XX. Racemic and chiral syntheses of the Alangium alkaloids 9-demethylprotoemetinol and 10-demethylprotoemetinol." @default.
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- W2046830939 doi "https://doi.org/10.1248/cpb.35.2755" @default.
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