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Issue 26, 2016
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Asymmetric synthesis and absolute stereochemistry of a labdane-type diterpenoid isolated from the rhizomes of Isodan yuennanensis

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Abstract

The first synthesis of a labdane-type diterpenoid isolated from Isodon yuennanensis was achieved in fourteen steps from commercially available starting material, (+)-sclareolide. The synthesis features the Barton nitrite ester reaction to introduce an oxime at the angular methyl group and the Jones oxidation to construct the lactone segment. By comparison of the optical rotation of our synthetic sample and the natural sample, the absolute stereochemistry of the natural diterpenoid has been determined.

Graphical abstract: Asymmetric synthesis and absolute stereochemistry of a labdane-type diterpenoid isolated from the rhizomes of Isodan yuennanensis

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Publication details

The article was received on 08 Apr 2016, accepted on 18 May 2016, published on 18 May 2016 and first published online on 18 May 2016


Article type: Paper
DOI: 10.1039/C6OB00750C
Citation: Org. Biomol. Chem., 2016,14, 6225-6230
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    Asymmetric synthesis and absolute stereochemistry of a labdane-type diterpenoid isolated from the rhizomes of Isodan yuennanensis

    H. Deng, W. Cao, Z. Zhang and B. Liu, Org. Biomol. Chem., 2016, 14, 6225
    DOI: 10.1039/C6OB00750C

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