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Semisynthesis and biological evaluation of abietane-type diterpenes. Revision of the structure of rosmaquinone

Abstract:

The new aromatic diterpenes 7β-O-benzylrosmanol (3), 7β-O-benzyl-11,12-di-O-methylrosmanol (4), and 7α-thiophenylcarnosic acid (5) have been obtained by partial synthesis from carnosol (1), an abundant natural diterpene present in Salvia species. The structures of these compounds were established from their physical and spectroscopic data. The known diterpenes sagequinone methide A (6), 7β-O-methylrosmanol (7), 7-O-methylrosmanol (8), and rosmaquinone B (9) were obtained from rosmanol (2). The spectroscopic data of these semisynthetic diterpenes were identical to data reported in the literature. In addition, the new semisynthetic isorosmaquinone (10) was obtained from isorosmanol (12). The proton resonances of rosmaquinone (11) are reassigned based on 2D NMR spectroscopy. These compounds, as well as eight known analogues, were evaluated for cytotoxic and antimicrobial activities. © 2009 American Chemical Society and American Society of Pharmacognosy.