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Mitragyna alkaloids: the structure of stipulatine

✍ Scribed by James B. Hendrickson; James J. Sims

Publisher
Elsevier Science
Year
1963
Tongue
French
Weight
294 KB
Volume
4
Category
Article
ISSN
0040-4039

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✦ Synopsis

In cularly examine connection with our interest in Hitragyna alkaloids and partithe unusual k-methoxy-indole mitragynine (2) , we had occasion to two batches of N. pciosa, collected six months apart on Luzon in the phillippines and another collected on Mindanao. Mitragynine was reported (3) found in this species in Borneo but no trace of it was found in our samples. From the bark and leaves of the latter, however, we have succeeded in isolating by the usual procedure Ck) rhynocophylline (Id)(5) and a new alkaloid named stipulatine from its discovery first in the leaves of r. rubrostipulata. jJe have assigned the structure Ia to this alkaloid as follows. Stipulatine (C,,H,~N,O,, pKa (SG$ EtCH) 5.2, [o]i6*6 = +lcS*+-10 (CHCls), m.p. 238-bO")(6) was shown to contain two methoxyl functions by

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