Convergent Total Synthesis of (+/-)-Apomorphine via Benzyne Chemistry: Insights into the Mechanisms Involved in the Key Step

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2017
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Muraca, Ana Carolina A. [UNIFESP]
Perecim, Givago P. [UNIFESP]
Rodrigues, Alessandro [UNIFESP]
Raminelli, Cristiano [UNIFESP]
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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.
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Synthesis-Stuttgart. Stuttgart, v. 49, n. 16, p. 3546-3557, 2017.
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