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Total synthesis of orientalol F via gold-catalyzed cycloisomerization of alkynediol

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Abstract

The total synthesis of orientalol F has been achieved starting from 1,4-dioxaspirodecan-8-one 11 in 13 steps. The key steps in this synthesis feature: (1) gold-catalyzed tandem cycloisomerization of alkynediol 10 for the formation of its seven-membered oxa-bridged bicyclic skeleton 9 of orientalol F, (2) visible-light-promoted organocatalytic aerobic oxidation of silyl enol ether 16 to enone 17, (3) Barbier-type butenylation for the diastereoselective synthesis of allylic alcohol 18 from enone 17, and (4) substrate-controlled Pd-catalyzed hydrogenation of 20 for the stereoselective installation of the C1 stereogenic center of 8.

Graphical abstract: Total synthesis of orientalol F via gold-catalyzed cycloisomerization of alkynediol

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Publication details

The article was received on 28 Jul 2017, accepted on 23 Aug 2017 and first published on 25 Aug 2017


Article type: Research Article
DOI: 10.1039/C7QO00654C
Citation: Org. Chem. Front., 2017, Advance Article
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    Total synthesis of orientalol F via gold-catalyzed cycloisomerization of alkynediol

    Y. Gu, J. Huang, J. Gong and Z. Yang, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00654C

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