| Full text | |
| Author(s): |
Muraca, Ana Carolina A.
;
Perecim, Givago P.
;
Rodrigues, Alessandro
;
Raminelli, Cristiano
Total Authors: 4
|
| Document type: | Journal article |
| Source: | SYNTHESIS-STUTTGART; v. 49, n. 16, p. 3546-3557, AUG 2017. |
| Web of Science Citations: | 4 |
| Abstract | |
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. (AU) | |
| FAPESP's process: | 15/09984-9 - Development of new routes for preparation of aryne precursors with application in stereoselective syntheses of bioactive alkaloids |
| Grantee: | Cristiano Raminelli |
| Support Opportunities: | Regular Research Grants |