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- W2036508730 abstract "Total syntheses are described for seven tacamine-type indole alkaloids (1–7) found in Tabernaemontana eglandulosa. (±)-Tacamine (1), (±)-16-epitacamine (2), and (±)-apotacamine (3) were prepared from pentacyclic intermediates 18. Apotacamine (3) was also obtained from aldehyde 12 via epimerization of 20-epiapotacamine (19) by the Polonovski-Potier reaction. Homologation of ester 13 led to 20-epitacamonine (23), which was similarly converted to (±)-tacamonine (4). Reduction of 4 gave (±)-descarbomethoxytacamines 5 and 6. Aldehyde 11 was reacted with trimethylsilyl cyanide (TMSCN) to yield the two (±)-17-hydroxytacamonines (7), of which the isomer with an axial hydroxy group (17β-OH) was found to be identical with the natural compound. Finally, an attempt to prepare (±)-19S-hydroxytacamine (8) is described. As an intermediated for this, a new synthesis of the pyridine alkaloid methyl 5-(1′-hydroxyethyl)nicotinate (34) was achieved." @default.
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- W2036508730 date "1996-08-01" @default.
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- W2036508730 title "Total syntheses of tacamine-type indole alkaloids of Tabernaemontana eglandulosa" @default.
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- W2036508730 doi "https://doi.org/10.1016/0040-4020(96)00663-1" @default.
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