Synthesis of C-homoaporphines via microwave-assisted direct arylation

TETRAHEDRON

卷:67

Article

Chaudhary, Sandeep¹  Harding, Wayne W.¹ 

[1] CUNY Hunter Coll, Dept Chem, New York, NY 10065 USA

关键词: Homoaporphine;    Aporphine;    Alkaloid;    Microwave-assisted;    Direct arylation;   

DOI  :  10.1016/j.tet.2010.11.059

来源: Elsevier

【 摘 要 】

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. (C) 2010 Elsevier Ltd. All rights reserved.

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