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Aldehyde Intermediates in the Synthesis of Tacamine-Type Indole Alkaloids: Preparation of (±)-apotacamine

✍ Scribed by Arto Tolvanen; David Din Belle; Mauri Lounasmaa

Publisher: John Wiley and Sons
Year: 1994
Tongue: German
Weight: 394 KB
Volume: 77
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19940770314

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✦ Synopsis

Abstract

The synthesis of aldehyde intermediates suitable for the preparation of indole alkaloids of the tacamine (1) type is described. The four possible aldehydes 4–7 were prepared from methyl 5‐ethylnicotinate (8) in a few simple steps using a base‐catalyzed epimerization as the final step (Schemes 1 and 2). The key aldehyde 4, which is an analogue of the important vincamine intermediate 3 (‘Oppolzer's aldehyde’), was finally converted into the indole alkaloid (±)‐apotacamine (21).

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