Semisynthesis of rosmanol and its derivatives. Easy access to abietatriene diterpenes isolated from the genus Salvia with biological activities.
The known diterpenes rosmanol (3), rosmaquinone (4), 7-methoxyrosmanol (5), 7-ethoxyrosmanol (6), galdosol (7), and epirosmanol (8) have been obtained by partial synthesis from carnosol (2), an abundant natural product present in Salvia species. The physical and spectroscopic data of these semisynthetic diterpenes were identical to those of authentic natural samples and with data reported in the literature. These abietane diterpenes have very interesting biological activities and are present in the genus Salviain low quantities; thus, the semisynthetic approach described here represents an efficient alternative method to obtain these compounds. Additionally, the known diterpene 16-hydroxyrosmanol (10) and a new aromatic diterpene 11 were obtained from 16-hydroxycarnosol (9) by reaction with Ph3P/NBS in CH2Cl2. The structure of the new compound 11 was established from its spectroscopic data as 12,16-epoxycarnosol.
Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna, Avenida Astrofísico Francisco Sánchez 2, 38206 La Laguna, Tenerife, Canary Islands, Spain.
Joaquín G
JG
Marrero
Lucía S
LS
Andrés
Javier G
JG
Luis
D045784:Abietanes; D002384:Catalysis; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D010616:Phenanthrenes / Q000138:chemical synthesis / Q000737:chemistry; D010936:Plant Extracts / Q000138:chemical synthesis / Q000737:chemistry; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D027544:Salvia / Q000737:chemistry*
D045784:Abietanes; D004224:Diterpenes; D010616:Phenanthrenes; D010936:Plant Extracts; C465582:rosmaquinone; C068623:carnosol; C465581:rosmanol; C018381:salvin