863203-28-5Relevant academic research and scientific papers
Diastereoselective routes towards the austrodorane skeleton based on pinacol rearrangement: synthesis of (+)-austrodoral and (+)-austrodoric acid
Alvarez-Manzaneda, Enrique,Chahboun, Rachid,Barranco, Inmaculada,Cabrera, Eduardo,Alvarez, Esteban,Lara, Armando,Alvarez-Manzaneda, Ramón,Hmamouchi, Mohamed,Es-Samti, Hakima
, p. 11943 - 11951 (2007)
Efficient routes towards the austrodorane skeleton from the labdane diterpene (-)-sclareol (22) are described. The processes, based on pinacol rearrangement, take place with complete diastereoselectivity. Utilizing these, the marine nor-sesquiterpenes (+)-austrodoral (1) and (+)-austrodoric acid (2) have been prepared from 22. Ketone 19, a key intermediate in the synthesis of rearranged cytotoxic diterpene lactones, such as norrisolide (3), has also been prepared in moderate yield.
First enantiospecific synthesis of marine nor-sesquiterpene (+)-austrodoral from (-)-sclareol
Alvarez-Manzaneda,Chahboun,Barranco,Cabrera Torres,Alvarez,Alvarez-Manzaneda
, p. 5321 - 5324 (2007/10/03)
A short and efficient synthesis of the rearranged nor-sesquiterpenes (+)-austrodoral (1) and (+)-austrodoric acid (2), recently isolated from the Antarctic marine mollusk Austrodoris kerguelenensis, from diterpene (-)-sclareol (4) is reported. The key step of the sequence is the pinacol rearrangement of the drimanetriol 11.
