Synthesis of C-Homoaporphines via Microwave-Assisted Direct Arylation.
Chaudhary S1, Harding WW.
Tetrahedron. 2011 Jan 21;67(3):569-575.
Representatives of the C-homoaporphine class of alkaloids have shown interesting biological activities. To date the synthesis of these molecules has never been attempted via a direct arylation strategy. We report herein the first Pd-mediated intramolecular direct arylation in the synthesis of C-homoaporphines via the use of microwaves. Use of tricyclohexylphosphine tetrafluoroborate as ligand gave good percentage conversions and suppressed competing debromination with the substrates evaluated. This arylation strategy should be broadly useful in the synthesis of C-homoaporphine alkaloids as demonstrated herein in the synthesis of (±)-homonantenine.
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