1514644-93-9Relevant academic research and scientific papers
Synthetic studies of alkaloids containing pyrrolidine and piperidine structural motifs
Bhat, Chinmay
, p. 192 - 196 (2015/04/27)
Avenues to asymmetric alkaloids! Various 2-substituted pyrrolidine and piperidine chiral bioactive natural products were synthesized using a 'chiral pool' method. l-proline and l-pipecolinic acids with one chiral center served as the best precursors for the synthesis of these alkaloids. Overall, 14 total synthetic and 11 formal synthetic approaches were developed.
A concise diastereoselective approach to (+)-dexoxadrol, (-)-epi-dexoxadrol, (-)-conhydrine and (+)-lentiginosine from (-)-pipecolinic acid
Bhat, Chinmay,Tilve, Santosh G.
, p. 10876 - 10883 (2014/01/06)
A new diastereoselective pathway for the total synthesis of (+)-dexoxadrol, first asymmetric synthesis of (-)-epi-dexoxadrol and formal synthesis of conhydrine and (+)-lentiginosine is presented using commercially available (-)-pipecolinic acid. The key reactions utilized are Sharpless asymmetric dihydroxylation and Wittig reaction. The paper further describes the study of effect of protecting groups on dihydroxylation of a terminal olefin in piperidine ring system.
