77515-67-4Relevant academic research and scientific papers
Studies on the Synthesis of 1-Azaspiroundecanes Related to Histrionicotoxin
Venit, John J.,DiPierro, Michael,Magnus, Philip
, p. 4298 - 4301 (2007/10/02)
3-Methoxybenzaldehyde was converted into 4-(3-methoxyphenyl)butylamine (4), and the derived hydrochloride was reduced with Li/NH3/EtOH to give the spirocyclic keto amine 6.The reduction of 6 and urethane derivatives 13 and 14 to give the corresponding cis and trans alcohols 9/10, 15/16, and 17/18 was studied.The keto amine 6 upon attempted ketalization underwent rearrangement to give the α,β-unsaturated imine 11.Treatment of 6 with N-chlorosuccinimide, followed by DBU, gave the aziridine 21.The amide 25 was converted derectly into 1-azaspiroundecane-2,8-dione (24) by Birch reduction and acid hydrolysis.The dione 24 underwent stereospecific reduction with LS-Selectride to give the cis alcohol 30.
STUDIES ON HISTRIONICOTOXIN: REARRANGEMENT OF THE SPIROCYCLIC HISTRIONICOTOXIN CARBON SKELETON INTO THE FUSED PUMILIOTOXIN SKELETON
Venit, John J.,Magnus, Philip
, p. 4815 - 4818 (2007/10/02)
On the treatment with acid the spirocyclic ketoamine 5 undergoes a retro-Mannich reaction followed by recondensation to give the unsaturated imine 8, thus converting the histrionicotoxin carbon skeleton into the pumiliotoxin C skeleton.
