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Syntheses in the series of lycopodium alkaloids III. A novel system active in photochemical additions

✍ Scribed by E.H.W. Bőhme; Z. Valenta; K. Wiesner

Publisher: Elsevier Science
Year: 1965
Tongue: French
Weight: 152 KB
Volume: 6
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)84003-x

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✦ Synopsis

In continuation of our efforts to develop methods of potential usefulness in the synthesis of Iycopodium alkaloids, we have turned our attention to annotinine I (1). A priori, the best entry into the system of this compound seemed a Beckmann rearrangement of an oxime of the type II obtainable from the corresponding ketone which in turn is a photoadduct of propenn and the cyclopentenone III. The model compound (II, R,, R, = H) was easily obtained (3) but the Beckmann rearrangement, while yielding some of the lactam IV, was unpromising.

Consequently, we have decided to synthesize the system V and to investigate its behaviour in photoadditions.

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