@article{oai:kanazawa-u.repo.nii.ac.jp:00014768, author = {Fujii, Tozo and Ohba, Masashi}, issue = {10}, journal = {Chemical & pharmaceutical bulletin}, month = {Oct}, note = {The racemic synthesis of the Alangium lamarckii alkaloid 10-demethyltubulosine (2) has been accomplished for the first time via a "lactim ether route, "which included the intermediates (±)-7,(±)-8,(±)-10,and (±)-9. The 1'α-H isomers (±)-12 and (±)-11 were also obtained through this synthetic route. The assignments of the configuration at C-1'of (±)-2,(±)-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. The identity of synthetic (±)-2 with (-)-demethyltubulosine from A. lamarckii unequivocally established the structure of this alkaloid.}, pages = {4314--4319}, title = {Quinolizidines. XV. A Racemic Synthesis of 10-Demethyltubulosine, an Alkaloid from Alangium lamarckii}, volume = {33}, year = {1985} }