169129-35-5Relevant academic research and scientific papers
Intramolecular carbolithiation reactions for the preparation of 3-alkenylpyrrolidines.
Coldham, Iain,Price, Kathy N,Rathmell, Richard E
, p. 2111 - 2119 (2007/10/03)
Tin-lithium exchange allows the formation of alpha-amino-organolithium species that undergo anionic cyclization onto allylic ethers to give 3-alkenylpyrrolidines. The methodology has been applied to the synthesis of an advanced intermediate related to the natural product (-)-alpha-kainic acid.
An efficient and stereoselective construction of the core structure of the manzamines via an intramolecular Michael reaction
Brands,DiMichele
, p. 1677 - 1680 (2007/10/03)
A strategically functionalized tricyclic subunit of the manzamines was efficiently synthesized with complete stereochemical control using a combination of an intramolecular Michael reaction of a pyroglutamic acid derivative and a hydrogenation.
Mannich biscyclizations. Total synthesis of (-)-ajmalicine
L?gers, Michael,Overman, Larry E.,Welmaker, Gregory S.
, p. 9139 - 9150 (2007/10/02)
A concise enantioselective total synthesis of the cardiovascular agent (-)-ajmalicine and an approach toward the synthesis of (+)-19-epiajmalicine are described. The key step of the (-)-ajmalicine synthesis is a carboxylate-terminated N-acyliminium ion biscyclization (74 → 67), which assembles the D and E rings of this heteroyohimbine alkaloid in one step. A related carboxylate-terminated iminium ion biscyclization (28 → 29) is the central step in the approach to (+)-epiajmalicine.
