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

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

Author Muraca, Ana Carolina A. Autor UNIFESP Google Scholar
Perecim, Givago P. Autor UNIFESP Google Scholar
Rodrigues, Alessandro Autor UNIFESP Google Scholar
Raminelli, Cristiano Autor UNIFESP Google Scholar
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.
Keywords (+/-)-apomorphine
aporphine core
benzyne chemistry
mechanisms
NMR experiments
theoretical calculations
Language English
Sponsor Sao Paulo Research Foundation (FAPESP) [2015/09984-9]
FAPESP
Coordination for the Improvement of Higher Education Personnel (CAPES)
CAPES
Date 2017
Published in Synthesis-Stuttgart. Stuttgart, v. 49, n. 16, p. 3546-3557, 2017.
ISSN 0039-7881 (Sherpa/Romeo, impact factor)
Publisher Georg Thieme Verlag Kg
Extent 3546-3557
Origin http://dx.doi.org/10.1055/s-0036-1588855
Access rights Closed access
Type Article
Web of Science ID WOS:000407139300003
URI http://repositorio.unifesp.br/handle/11600/51451

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