Quinolizidines. XIV. A racemic synthesis of 9-demethyltubulosine, an alkaloid isolated from Alangium vitiense

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The first total synthesis of the Alangium vitiense alkaloid 9-demethyltubulosine (1) has been achieved in the form of a racemic modification through a"lactim ether route, " which included the intermediates (±)-7,(±)-8,(±)-10,and (±)-9. The 1'α-Hisomers (±)-12 and (±)-11 were also produced through this synthetic route. On the other hand, the nonconformity of synthetic (±)-1 with another (-)-demethyltubulosine from A. lamarckii indicated the alternative 10-demethyl structure (2) to be correct for the A. lamarckii alkaloid. The assignments of the configuration at C-1' of (±)-1,(±)-9,(±)-11,and (±)-12 were based on four criteria, namely, the ratio of products from the catalytic reduction of (±)-10,thin-layer chromatographic mobility, and ^1H and ^<13>C nuclear magnetic resonance spectral features.
公益社団法人日本薬学会の論文
1985-09-25