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Programmed serial stereochemical relay and its application in the synthesis of morphinans

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Abstract

Herein we report a rationally designed, serial point-to-axial and axial-to-point stereoinduction and its integration into multi-step and target-oriented organic synthesis. In this proof-of-concept study, the configurational stability of several carefully designed atropisomeric intermediates and the fidelity of their unconventional stereoinductions were systematically investigated. The highly functionalized prepared synthetic intermediate was further applied in a novel chemical method to access the morphinans and it is potentially applicable to other structurally related alkaloids.

Graphical abstract: Programmed serial stereochemical relay and its application in the synthesis of morphinans

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Publication details

The article was received on 21 Jul 2017, accepted on 15 Aug 2017 and first published on 30 Aug 2017


Article type: Edge Article
DOI: 10.1039/C7SC03189K
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY license
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    Programmed serial stereochemical relay and its application in the synthesis of morphinans

    K. Ho (Kenny) Park, R. Chen and D. Y.-K. Chen, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C7SC03189K

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