Abstract
The partial synthesis of derivatives of the antimicrobial diterpenoid rosmic acid from the abundant diterpenoid car-nosol is described. The key step involved the cleavage of ring C of rosmanol with lead tetraacetate or 7-O-methylrosmanol with mCPBA. Three analogues of rosmic acid, 11,12-seco-8,13-abietadien-12,7:20,6β-dilacton-11-oic acid methyl ester, 7α-O-methyl-11,12-seco-11,12-epoxy-11,12-dioxo-8,13-abietadien-20,6β-olide, its dimethyl ester, and the known methylgaldosol and rosmaquinone were obtained.
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