Literature DB >> 14535817

A facile asymmetric route to (-)-aphanorphine.

Hongbin Zhai1, Shengjun Luo, Chengfeng Ye, Yongxiang Ma.   

Abstract

8O-methylaphanorphine was synthesized from 4-methoxyphenylacetaldehyde in 36% overall yield and in nine steps, featuring the formation of ring B via a Friedel-Crafts alkylative cyclization with the concomitant stereospecific introduction of the benzylic quaternary carbon center. The current work constitutes an efficient enantioselective formal synthesis of 3-benzazepine marine alkaloid (-)-aphanorphine.

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Year:  2003        PMID: 14535817     DOI: 10.1021/jo0348726

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  4 in total

1.  Enantioconvergent synthesis of (+)-aphanorphine via asymmetric Pd-catalyzed alkene carboamination.

Authors:  Duy N Mai; Brandon R Rosen; John P Wolfe
Journal:  Org Lett       Date:  2011-05-10       Impact factor: 6.005

2.  6-Azabicyclo[3.2.1]octanes Via Copper-Catalyzed Enantioselective Alkene Carboamination.

Authors:  Barbara J Casavant; Azade S Hosseini; Sherry R Chemler
Journal:  Adv Synth Catal       Date:  2014-08-11       Impact factor: 5.837

3.  Recent Developments in Pd-Catalyzed Alkene Aminoarylation Reactions for the Synthesis of Nitrogen Heterocycles.

Authors:  Danielle M Schultz; John P Wolfe
Journal:  Synthesis (Stuttg)       Date:  2012       Impact factor: 3.157

4.  Production of benzazepine derivatives via four-component reaction of isatins: study of antioxidant activity.

Authors:  Fathali Gholami Orimi; Behrooz Mirza; Zinatossadat Hossaini
Journal:  Mol Divers       Date:  2020-06-10       Impact factor: 2.943

  4 in total

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