Journal
SYNTHESIS-STUTTGART
Volume 49, Issue 16, Pages 3546-3557Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1588855
Keywords
(+/-)-apomorphine; aporphine core; benzyne chemistry; mechanisms; NMR experiments; theoretical calculations
Categories
Funding
- Sao Paulo Research Foundation (FAPESP) [2015/09984-9]
- FAPESP
- Coordination for the Improvement of Higher Education Personnel (CAPES)
- CAPES
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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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