Convergent Total Synthesis of (±)-Apomorphine via Benzyne Chemistry: Insights into the Mechanisms Involved in the Key Step
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.
Muraca, Ana Carolina A.,Perecim, Givago P.,Rodrigues, Alessandro,Raminelli, Cristiano
supporting information
p. 3546 - 3557
(2017/08/15)
Tetrabutylammonium phthalimide-N-oxyl: An efficient organocatalyst for trimethylsilylation of alcohols and phenols with hexamethyldisilazane
Tetrabutylammonium phthalimide-N-oxyl (TBAPINO) was found to be an effective organocatalyst for rapid, simple and chemoselective protection of the hydroxyl group of alcohols and phenols using hexamethyldisilazane (HMDS) under mild conditions. The low catalyst loading, high to quantitative yields and simple removal of the catalyst from the reaction mixture illustrate the other attractive features of this protocol.
Dekamin,Yazdaninia,Mokhtari,Naimi-Jamal
experimental part
p. 537 - 544
(2012/06/18)
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