✦ LIBER ✦
β-Carbolin-Alkaloide, II Tributyl(1-ethoxyvinyl)stannan als C2-Baustein für die Synthese von β-Carbolin-Alkaloiden
✍ Scribed by Bracher, Franz ;Hildebrand, Dirk
- Publisher
- John Wiley and Sons
- Year
- 1993
- Tongue
- English
- Weight
- 266 KB
- Volume
- 1993
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
β‐Carboline Alkaloids, II. – Tributyl(1‐ethoxyvinyl)stannane as a C~2~‐Building Block in the Syntheses of β‐Carboline Alkaloids
1‐Acetyl‐β‐carboline (4) is prepared by palladium‐catalyzed coupling of 1‐chloro‐β‐carboline (1) with tributyl(1‐ethoxyvinyl)stannane (3) and subsequent hydrolysis with aqueous acid. Reduction of 4 with NaBH~4~ gives the alkaloid 5. Nitramarine (7) and annomontine (9) are prepared from 4 by one‐pot conversions of the acetyl group to a quinoline or an aminopyrimidine ring, respectively.