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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.