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DOI: 10.1055/s-0036-1588855
Convergent Total Synthesis of (±)-Apomorphine via Benzyne Chemistry: Insights into the Mechanisms Involved in the Key Step
We are grateful to São Paulo Research Foundation (FAPESP) for financial support (Grant No. 2015/09984-9). A.C.A.M thanks FAPESP and Coordination for the Improvement of Higher Education Personnel (CAPES) and G.P.P. thanks CAPES for their fellowships.Publikationsverlauf
Received: 18. März 2017
Accepted after revision: 04. Mai 2017
Publikationsdatum:
20. Juni 2017 (online)
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.
Key words
(±)-apomorphine - aporphine core - benzyne chemistry - mechanisms - NMR experiments - theoretical calculationsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588855.
- Supporting Information
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