Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 20, Pages 10033-10040Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01634
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- Fundacao de Amparo a Pesquisa do Estado de Sao Paulo, Brazil (FAPESP)
- CAPES
- FAPESP
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Total syntheses of lysicamine, (+/-)-nuciferine, (+/-)-nomuciferine, (+/-)-zanthoxyphylline iodide, (+/-)-O-methylisothebaine, and (+/-)-trimethoxynoraporphine were accomplished by an approach that involves the formation of aporphine cores through reactions between an isoquinoline derivative and silylaryl triflates promoted by CsF. Unprecedented formations of aporphine cores proceeded in good yields presumably through [4 + 2] cycloaddition reactions followed by hydrogen migrations.
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