886038-15-9Relevant academic research and scientific papers
Total synthesis of the marine alkaloid (±)-lepadiformine via a radical carboazidation
Schaer, Pascal,Renaud, Philippe
, p. 1569 - 1571 (2007/10/03)
The total synthesis of lepadiformine has been achieved in 10 steps and 15% overall yield from cyclohexanone. The amino-substituted quaternary carbon center is created through a radical carboazidation reaction. The tricyclic core of lepadiformine is built via an efficient hydrogenation process, involving reduction of the azide and intramolecular reductive amination of a ketone, followed by lactamization of the intermediate γ-aminoester. The hydroxymethyl side chain is introduced according to a modified Takahata procedure after conversion of the lactam into a thiolactam.
Synthetic studies on the perhydropyrrolo[2,1-j]quinoline marine alkaloids lepadiformine and cyclindricine C using a 2-azapentadienyl anion cycloaddition. Synthesis of 2,13-diepilepadiformine (or 2-epi-11-deoxycylindricine C)
Pearson, William H.,Barta, Nancy S.,Kampf, Jeff W.
, p. 3369 - 3372 (2007/10/03)
Tin-lithium exchange of 13 with n-BuLi produced the 2-azapentadienyl anion 6 (R = CH3), which participated in a [π4s+π2s] cycloaddition reaction with phenyl vinyl sulfide to afford the spirocyclic pyrrolidine 14, which as coverted to 2,13-diepi
