Studies on intramolecular alkylation. IX the synthesis of tricyclic dienones suitable for the synthesis of 13-hydroxygibberellins
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2- Hydroxy-6-methoxy-l, 2, 3, 4-tetrahydro-2-naphthoic acid and its 8-methoxy isomer were converted into trichloroacetate and dichloroacetate derivatives and thence to diazoketones (2), (3), (12) and (13). The acid-catalysed cyclization of these substrates to the dienones (6), (7), (16) and (17), respectively, was then studied. The trichloroacetoxy derivatives gave the best yields of dienones.
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Australian Journal of Chemistry