A new route toward 7-Oxo-13-hydroxy-8,11,13-podocarpatrienes from labdane diterpenes.
Trinorlabdane 1,5-diketones (7, 10a,b, 13a,b), which are easily prepared from labdane diterpenes, are directly converted into the corresponding 7-oxo-13-hydroxy-8,11,13-podocarpatrienes, immediate precursors of bioactive compounds, under basic treatment. Utilizing this strategy, the first enantiospecific synthesis of 13-hydroxy-8,11,13-podocarpatriene (20), a constituent of Taiwania cryptomerioides, was achieved starting from (-)-sclareol (5) after a seven-step sequence in 55% overall yield.
Alvarez-Manzaneda Roldán
Enrique
E
Departamento de Química Organica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, Spain. eamr@ugr.es
Romera Santiago
Juan Luis
JL
Chahboun
Rachid
R
D045784:Abietanes / Q000737:chemistry* / Q000145:classification; D002384:Catalysis; D004224:Diterpenes / Q000138:chemical synthesis* / Q000145:classification; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry
D045784:Abietanes; D004224:Diterpenes; D007659:Ketones