Abstract
Functionalization of the
isopropyl group of methyl abieta-8,11,13- trien-18-oate (8) has been achieved by intramolecular
cyclizations of the 12-carboxy derivative (10) with lead tetraacetate and by
thermolysis of the diazomethyl ketone (11). ��� Nitration of methyl 12-acetylabieta-8,11,13-trien-18-oate
(9) has given the products (21) and (30), arising from nitrodeacylation and
nitrodealkylation reactions, respectively. The nitro ketone (30) has been
converted into methyl 13-hydroxypodocarpa-8,11,13-trien-18-oate
(38) in 26% overall yield from the ester (8). Birch reduction of the methyl
ether of the phenol (38) afforded the enone (50), a potentially useful
intermediate for synthesis.
Cited by
49 articles.
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