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Asymmetric synthesis of ent-fragransin C1

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Abstract

The first asymmetric synthesis of ent-fragransin C1 was reported. The key step involves an intramolecular C–O bond formation (furan ring formation) via chemoselective generation of the benzylic carbocation leading to the 2,3-anti-3,4-syn-4,5-anti-tetrahydrofuran moiety as a single diastereomer in good yield. Our synthesis confirms that ent-fragransin C1 possesses 2R,3R,4S,5S configurations.

Graphical abstract: Asymmetric synthesis of ent-fragransin C1

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Publication details

The article was received on 27 Mar 2017, accepted on 17 Apr 2017 and first published on 19 Apr 2017


Article type: Paper
DOI: 10.1039/C7OB00749C
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Asymmetric synthesis of ent-fragransin C1

    S. Chaimanee, M. Pohmakotr, C. Kuhakarn, V. Reutrakul and D. Soorukram, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB00749C

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