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Nucleophilic Acylation of 3,4-Dihydroisoquinolinium Salts. Diastereoselective Synthesis of the Protoberberine Alkaloid (±)-Corydaline and of Analogous Compounds

✍ Scribed by Tietze, Lutz F. ;Brill, Gunter

Publisher: John Wiley and Sons
Year: 1987
Tongue: English
Weight: 885 KB
Volume: 1987
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.198719870327

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✦ Synopsis

NucleophiLic acylation of 3,44ihydroisoquinoliniinolinium salts 3 with lithiated enol ethers 6, 7, and 8 or vinyl sulfides 14 leads to the adducts 4 9 , and 16, mpctively, in mostly excellent yields. Hydrolysis of 4 alTords 94-97% of the ketones 5, which are transformed by treatment with conc. hydrochloric acid and successive reduction with NaH3BCN via the enamines 18 into the dibenzoquinolizidines 19; thus Sb gives (ftcorydaline (2 = 19b) in 84% yield.

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