Decaryiol, a New Cembrane Diterpene from the Marine Soft Coral Sarcophyton decaryi

Article abstract of DOI:10.1021/jo00334a036

The petroleum ether extract of the soft coral Sarcophyton decaryi yielded the cembrane-type diterpenes thunbergol (1), decaryiol (4), and 3,4-epoxynephthenol (13) in addition to nephthenol and trocheliophorol as reported previously.Compounds 4 and 13 are new and were characterized by spectral data, degradative studies by ozonolysis, and chemical transformations.Nephthenol reacts with tetrabromocyclohexadienone to give 11, the 3-bromo analogue of decaryiol.Compounds 4 and 11 rearrange to an enol ether (10), thereby proving the cembranoid structure of 4. 3,4-Epoxynephthenol (13), the second new cembranoid, is believed to be the biogenetic precursor of decaryiol (4), and, indeed, 13 could be transformed into 4 by acid catalysis.