Journal of the Chemical Society. Perkin transactions I p. 1273 - 1277 (1981)
Update date:2022-08-04
Topics:
Prabhakar, Sundaresan
Lobo, Ana M.
Tavares, M. Regina
Oliveira, Ilda M. C.
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).
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