期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 49, 页码 13498-13501出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201408435
关键词
alkaloids; asymmetric synthesis; oxidative coupling; total synthesis
资金
- EPSRC [EP/I002065/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/I002065/1] Funding Source: researchfish
A gram-scale catalytic enantioselective formal synthesis of morphine is described. The key steps of the synthesis involve an ortho-para oxidative phenolic coupling and a highly diastereoselective desymmetrization of the resulting cyclohexadienone that generates three of the four morphinan ring junction stereocenters in one step. The stereochemistry is controlled from a single carbinol center installed through catalytic enantioselective hydrogenation. These transformations enabled the preparation of large quantities of key intermediates and could support a practical and scalable synthesis of morphine and related derivatives.
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