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β‐Carbolin‐Alkaloide, II Tributyl(1‐ethoxyvinyl)stannan als C 2 ‐Baustein für die Synthese von β‐Carbolin‐Alkaloiden
Author(s) -
Bracher Franz,
Hildebrand Dirk
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301132
Subject(s) - chemistry , stannane , quinoline , stereochemistry , medicinal chemistry , organic chemistry
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.