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The synthesis of a degradation product of ajaconine

✍ Scribed by J. Nabors; H. Miles; L.H. Zalkow

Publisher: Elsevier Science
Year: 1969
Tongue: French
Weight: 150 KB
Volume: 10
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)88186-7

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✦ Synopsis

In the course of the structure elucidation of ajaconine (I) a series of degradation products was prepared.

We wish now to report the SyntheBiS (as the enanticmer) of one of the key degradation products (II). This work provides synthetic confirmation for the I II location of the oxygen substituent at C-7 which heretofore has been based entirely on spectral data. In addition, it illustrates a basic sequence which with a few modification8 can be applied to the synthesis of ajaconine itself.

Adduct III, prepared a8 previously described from podocarpic acid*, wae treated with sodium carbonate in aqueous methanol to give IV, which on Kiliani oxidation gave V.

Esterification of the latter with ethereal diazomethane gave triester VI [m.p. l.

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