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The regiospecific synthesis of the A and B rings of phomazarin
Author(s) -
Guay Vincent,
Brassard Paul
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.5570240629
Subject(s) - chemistry , hydroquinone , naphthoquinone , yield (engineering) , ring (chemistry) , stereochemistry , diene , substrate (aquarium) , lactam , organic chemistry , materials science , natural rubber , oceanography , metallurgy , geology
Elaboration of the A ring of phomazarin by the Conrad‐Limpach approach has been shown to be possible in the case of a protected hydroquinone substrate. However similar condensations using a suitably substituted naphthoquinone gave a lactam instead of the expected benzoquinolone. Attempts to annulate simplified models of the A‐B rings with the appropriate diene have also been successful albeit in low yield.