4965-16-6Relevant academic research and scientific papers
Convergent Total Synthesis of (±)-Apomorphine via Benzyne Chemistry: Insights into the Mechanisms Involved in the Key Step
Muraca, Ana Carolina A.,Perecim, Givago P.,Rodrigues, Alessandro,Raminelli, Cristiano
, p. 3546 - 3557 (2017/08/15)
Convergent total synthesis of (±)-apomorphine hydrochloride was accomplished by an approach that employs in the key step a sequence of transformations involving a [4+2]-cycloaddition reaction followed by a hydrogen migration. Through this sequence of transformations, the desired aporphine core was obtained regioselectively in 75% isolated yield. Since only one regioisomer was produced in the key step of the synthesis, a polar [4+2]-cycloaddition mechanism was proposed. Furthermore, NMR experiments and theoretical calculations were carried out to elucidate the hydrogen migration mechanism. (±)-Apomorphine hydrochloride was achieved after 9 steps in an overall yield of 8% involving benzyne chemistry.
A convenient formation of aporphine core via benzyne chemistry: Conformational analysis and synthesis of (R)-aporphine
Perecim, Givago P.,Rodrigues, Alessandro,Raminelli, Cristiano
, p. 6848 - 6851 (2015/11/27)
Total synthesis of (R)-aporphine has been accomplished by an approach that employs in the key step a sequence of transformations involving a [4+2] cycloaddition reaction followed by a hydrogen migration, leading to aporphine core in good yield, which was subjected to a 1D gradient NOE experiment, conformational analysis, and simple transformations, including a small scale resolution process, to afford enantiomerically enriched aporphine alkaloid.
Bioorganic Studies: Part IV - Reductive N-Acylation of Imines Using 3,5-Dicarbethoxy-2,6-dimethyl-1,4-dihydropyridine as NADH Model
Singh, Serjinder,Sharma, Vijay K.
, p. 1087 - 1088 (2007/10/02)
A one-step reductive acetylation of imines (II) using 3,5-dicarbethoxy-2,6-dimethyl-1,4-dihydropyridine (I) as NADH model is reported.The N-acetyliminium intermediates are reduced in situ by I to give N-acetylamines (IV).Reduction of species which stabili
