119736-64-0Relevant articles and documents
Short synthesis of noscapine, bicuculline, egenine, capnoidine, and corytensine alkaloids through the addition of 1-siloxy-isobenzofurans to imines
Soriano, Maria Del Pilar C.,Shankaraiah, Nagula,Santos, Leonardo Silva
scheme or table, p. 1770 - 1773 (2010/05/18)
A concise diastereotioselective strategy for the synthesis of noscapine, bicuculline, and egenine (1a-c), as well as capnoidine and corytensine (2a,b), was developed using diastereoselective addition of 1-siloxy-isobenzofurans 4a and 4b to iminium ion 5 in a one-pot approach. The synthesis features the use of imine 13 obtained through Bischler-Napieralsky reaction from amine 11. The addition of ionic liquids as addictives in the reactions afforded erythro configuration in major adduct compounds. The synthetic route can also be applied in the total synthesis of promising tubulin binding agent EM105 (3).
Synthetic and Stereochemical Studies on Phthalideisoquinoline Hemiacetals
Rozwadowska, Maria D.,Matecka, Dorota
, p. 287 - 289 (2007/10/02)
The two new phthalideisoquinoline hemiacetals rac-egenine (3) and rac-corytensine (4) are prepared by stereoselective DIBAL reduction of rac-bicuculline (1) and rac-adlumidine (2), respectively.The identity of egenine (3) with decumbensine as well as of corytensine (4) with epi-α-decumbensine and humosine A is postulated.The configuration around the anomeric center in natural (+)-egenine (3), (+)-corytensine (4) and (-)-narcotine hemiacetal (7) is deduced as (7'S), (7'R) and (7'R), respectively.