Issue 10, 2017

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.

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

Supplementary files

Article information

Article type
Edge Article
Submitted
21 Jul 2017
Accepted
15 Aug 2017
First published
30 Aug 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2017,8, 7031-7037

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, 8, 7031 DOI: 10.1039/C7SC03189K

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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