Abstract
Synthesis of five novel piperidine monoterpene alkaloids using the
iridoid glucoside antirrhinoside as a synthon is described. Two
strategies for their preparation were investigated: the first
possible pathway involved an intermediate diol from which the
piperidine ring was expected to be constructed via reaction of its
ditosylate with an amine; the second strategy involved a double
reductive amination as the key step to the piperidine ring, which
proved successful. The stereochemistry of C-5 and C-9 in the
obtained piperidine monoterpenes was the same as that reported for
alfa-Skytanthine, a known isolate from Skytanthus acutus
(Apocynaceae).
Original language | English |
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Journal | Journal of Natural Products |
Volume | 60 |
Pages (from-to) | 1012-1016 |
ISSN | 0163-3864 |
Publication status | Published - 1997 |