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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Programmed serial stereochemical relay and its application in the synthesis of morphinans
Kun Ho Kenny Park1, Rui Chen1, David Y-K Chen1
1Department of Chemistry , Seoul National University , Gwanak-1 Gwanak-ro, Gwanak-gu , Seoul 151-742 , South Korea .
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.
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