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Synthetic approaches to cularines. I. Phenolic oxidative coupling
Author(s) -
De Lera Angel Rodriguez,
Saá José M.,
Suau Rafael,
Castedo Luis
Publication year - 1987
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570240120
Subject(s) - chemistry , isoquinoline , reagent , borane , oxidative coupling of methane , yield (engineering) , oxidative phosphorylation , organic chemistry , medicinal chemistry , combinatorial chemistry , biochemistry , catalysis , materials science , metallurgy
Ferricyanide‐promoted biogenetic‐type phenolic oxidative coupling of an 8,3′‐dihydroxytetrahydrobenzyl‐isoquinoline 19a afforded the isomeric phenolic cularines 5 and 21. Vanadium oxytrifluoride oxidation of the N ‐borane complex of 19a afforded, regioselectively, the para ‐coupled product 21. Moreover, when this reagent was used on the monophenolic tetrahydrobenzylisoquinoline 19b protected as its N ‐borane complex, cularine 1 was regioselectively obtained in good yield. Other structural modifications and reagents were not successful.