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Issue 29, 2017
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Strategy towards the enantioselective synthesis of schiglautone A

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Abstract

Herein is described a convergent enantioselective route to an advanced intermediate in the synthesis of schiglautone A, a Schisandra triterpenoid with an unusual architecture. The synthetic route to this intermediate displaying 6 of the 7 stereocenters builds upon two fragments, an aldehyde elaborated from the Wieland–Miescher ketone, and a ketone. The preparation of the latter features a lithiation–borylation enzymatic resolution sequence, which led to the formation of the desired product with high enantio- and diastereoselectivities. After aldol coupling of the two fragments, the final quaternary stereocenter was installed by cyclopropane opening. The functionalized intermediate was isolated as a single diastereoisomer and thus offers a valuable starting point for further synthetic exploration.

Graphical abstract: Strategy towards the enantioselective synthesis of schiglautone A

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Publication details

The article was received on 28 Mar 2017, accepted on 04 Jul 2017 and first published on 04 Jul 2017


Article type: Paper
DOI: 10.1039/C7OB00766C
Citation: Org. Biomol. Chem., 2017,15, 6242-6256
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    Strategy towards the enantioselective synthesis of schiglautone A

    C. Le Chapelain, Org. Biomol. Chem., 2017, 15, 6242
    DOI: 10.1039/C7OB00766C

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