@article{oai:kanazawa-u.repo.nii.ac.jp:00014869,
 author = {Fujii, Tozo and Kogen, Hiroshi and Yoshifuji, Shigeyuki and Ohba, Masashi},
 issue = {5},
 journal = {Chemical & pharmaceutical bulletin},
 month = {May},
 note = {The first total synthesis of the Alangium alkaloid alangimarckine (8) has been accomplished in the form of a racemic modification by means of an initial coupling of the (±)-tricyclic amino acid 6 with tryptamine and succeeding steps proceeding through the intermediates (±)-7,(±)-10,and (±)-9. The 1'-epimers (±)-12 and (±)-11 were also produced in this reaction sequence. A parallel sequence of conversions starting with the (-)-tricyclic amino acid 6 yielded the chiral molecule (-)-8 via the intermediates (+)-7,(+)-10,and (+)-9,together with the 1'-epimer (-)-11 via (-)-12. The identity of the synthetic (-)-8 with natural alangimarckine unequivocally established the structure and absolute configuration of this alkaoid. The assignments of the configuration at C-1'of 8,9,11,and 12 were based on five criteria, namely, the ratio of products from the NaBH_4 reduction of (±)-10,thin-layer chromatographic mobility, and proton and carbon-13 nuclear magnetic resonance and circular dichroism spectroscopic features.},
 pages = {1946--1954},
 title = {Quinolizidines. XIII. Syntheses of (±)-and (-)-Alangimarckines},
 volume = {33},
 year = {1985}
}