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- W1500844186 abstract "The first total synthesis of alangicine (3), an Alangium lamarckii alkaloid, has been achieved in the form of a racemic modification by means of an initial alkaline hydrolysis of the (±)-tricyclic ester 6 and succeeding steps proceeding through the intermediates (±)-7, (±)-10, and (±)-9. A parallel synthetic route starting with the (-)-tricyclic ester 6, derived from (+)-cincholoipon ethyl ester (8), produced the chiral target molecule (+)-3 with alangicine unequivocally established the structure and absolute stereochemistry of this alkaloid. The 13C nuclear magnetic resonance spectra of (±)-alangicine (3) and the ipecac and Alangium alkaloid psychotrine (18) confirmed their endocyclic double bond structures in the dihydroisoquinoline moiety. Catalytic reductions of 11, (±)-12, and 15 using hydrogen and Pd-C were investigated, and the results have shown that hydrogenolysis of the benzyloxy group proceeds much faster than saturation of the endocyclic C=N bond." @default.
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- W1500844186 date "1983-01-01" @default.
- W1500844186 modified "2023-10-10" @default.
- W1500844186 title "Quinolizidines. VIII. Structure and synthesis of the Alangium alkaloid alangicine: Syntheses of (.+-.)- and (+)-alangicines." @default.
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- W1500844186 doi "https://doi.org/10.1248/cpb.31.2583" @default.
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