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

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.

SUBMITTER: Ho Kenny Park K

PROVIDER: S-EPMC5642196 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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

Ho Kenny Park Kun K Chen Rui R Chen David Y-K DY

Chemical science 20170830 10

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 t ...[more]

PMID: 29147530

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