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Synthesis of Eburnamine, Isoeburnamine, and Eburnamonine via a Spirocyclic Intermediate

✍ Scribed by Tse-Lok Ho; Chun-Kuei Chen

Publisher
John Wiley and Sons
Year
2005
Tongue
German
Weight
103 KB
Volume
88
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Racemic eburnamonine (1) was synthesized via 6, an intermediate possessing local symmetry. Cleavage of the cyclopentene subunit led to pentacyclic aldehydes 8a/8b which on subsequent borohydride and Wolff–Kishner reductions gave 12. The final steps included a RuCl~3~‐catalyzed periodate oxidation and pyridinium chlorochromate (PCC) oxidation. The penultimate intermediates were racemic eburnamine (2) and racemic isoeburnamine (3).

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