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Issue 16, 2014
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Biomimetic total synthesis of (±)-yezo'otogirin A

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Abstract

The total synthesis of yezo'otogirin A has been achieved via a biosynthetically-inspired strategy. Diastereoselective synthesis of pre-yezo'otogirin A, the proposed biosynthetic pre-cursor of yezo'otogirin A, was accomplished in eight steps from 3-ethoxy-2-cyclohexenone. A biomimetic oxidative radical cyclization was then used to construct the unique tricyclic ring system of yezo'otogirin A. The synthesis showcases the ability of biomimetic radical cyclizations to generate complex natural products from unprotected intermediates.

Graphical abstract: Biomimetic total synthesis of (±)-yezo'otogirin A

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Publication details

The article was received on 24 Jan 2014, accepted on 04 Mar 2014 and first published on 12 Mar 2014


Article type: Communication
DOI: 10.1039/C4OB00186A
Citation: Org. Biomol. Chem., 2014,12, 2519-2522
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    Biomimetic total synthesis of (±)-yezo'otogirin A

    H. C. Lam, K. K. W. Kuan and J. H. George, Org. Biomol. Chem., 2014, 12, 2519
    DOI: 10.1039/C4OB00186A

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