78081-69-3Relevant academic research and scientific papers
Total Synthesis of the Alkaloids (+/-)-Alpinigenine and (+/-)-cis-Alpinigenine
Prabhakar, Sundaresan,Lobo, Ana M.,Tavares, M. Regina,Oliveira, Ilda M. C.
, p. 1273 - 1277 (2007/10/02)
A stereoselective synthesis of the rhoeadine alkaloid (+/-)-cis-alpinigenine is described.Hofmann elimination of the known tetracyclic base (4) gave the trans-azecine (7) which afforded the diol (13) on oxidation with N-bromosuccinimide.Periodic acid cleavage of (13) yielded the dibenzaldehyde (14), which on photolysis resulted in the formation of (+/-)-cis-alpinigenine (20-30percent) and (+/-)-alpinigenine (1percent) involving endo (16) and exo (15) (4s+2s) intramolecular additions respectively of the intermediate photodienol-E (Scheme 1).
