66643-49-0Relevant articles and documents
Total synthesis of (±)-20: S -hydroxy-1,2-dehydro-pseudoaspidospermidine via a C-H activation/transannular cyclization strategy
Leitner, Christian,Gaich, Tanja
supporting information, p. 7451 - 7453 (2017/07/12)
A total synthesis to the pseudoaspidospermidine family via a C-H activation/transannular cyclization strategy has been accomplished. The applicability of this approach is showcased in the concise synthesis (ten steps) of (±)-20S-hydroxy-1,2-dehydro-pseudoaspidospermidine (4) starting from literature known compound 11. Via a joint synthetic sequence we were also able to address the related iboga alkaloid (±)-isovelbanamine (7) in nine steps. Key features of this synthesis are a transannular cyclization to generate the pseudoaspidospermidine skeleton (C-H activation) and a Witkop photocyclization reaction providing a 9-membered lactam. It is also worth mentioning that the joint synthetic sequence can be carried out on a multigram scale.
1,6-Dihydro-3(2H)-pyridinones. I. Facile Synthesis of N-Substituted 1,6-Dihydro-3(2H)-pyridinones
Iamanishi, Takeshi,Shin, Hiroaki,Hanaoka, Miyoji,Momose, Takefumi,Imanishi, Ichiro
, p. 3617 - 3623 (2007/10/02)
The first synthesis of the N-substituted 1,6-dihydro-3(2H)-pyridinones (4 and 16) is described. 1-Benzyl-1,2,3,6-tetrahydropyridine (9) was treated with ethyl chloroformate to give the urethane (6), which was oxidized to the epoxide (10) with perbenzoic a
