736143-59-2Relevant academic research and scientific papers
The palladium(0) Suzuki cross-coupling reaction as the key step in the synthesis of aporphinoids
Suau,Rico,Nájera,Ortiz-López,López-Romero,Moreno-Ma?as,Roglans
, p. 5725 - 5735 (2007/10/03)
We report a flexible approach to the total synthesis of 4,5-dioxoaporphines based on the palladium(0) catalyzed Suzuki cross-coupling of phenylboronic acids with sterically hindered 2-bromo phenyl acetates or bromo phenyl acetamides, followed by sequential bicyclization of biarylacetamides promoted by oxalyl chloride/Lewis acid. The reduction of 4,5-dioxoaporphines provides a chemoselective entry to aporphines, dehydroaporphines and 4-hydroxy- dehydroaporphines. A three-steps total synthesis for (±)-O,O′- dimethylapomorphine from readily accessible precursors is also reported.
