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The Structure of the Alkaloid Peduncularine. Communication no. 172 on organic natural products

✍ Scribed by Hans-Peter Ros; Rolf Kyburz; Nigel W. Preston; Rex T. Gallagher; I. Ralph C. Bick; Manfred Hesse

Publisher
John Wiley and Sons
Year
1979
Tongue
German
Weight
450 KB
Volume
62
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The revised structure 1 is put forward for peduncularine, the main alkaloid of Aristotelia peduncularis (Labill.) HOOK. F. (Elaeocarpaceae), on the basis of its spectroscopic properties and those of its degradation products, the Hofmann base 3 and the hydrogenation product 4. Structure 1 represents the relative configuration of the alkaloid.

Peduncularine belongs to the class of indole alkaloids with a monoterpene unit as the aliphatic portion. To our knowledge it constitutes the first example in which an isopropyl group has become detached from the terpene unit and occurs as a substituent on nitrogen.

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