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Issue 28, 2016
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Asymmetric synthesis of (+)-17-epi-methoxy-kauran-3-one through tandem oxidative polycyclization-pinacol process

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Abstract

A synthesis of (+)-17-epi-methoxy-kauran-3-one, an O-methylated isomer of the natural diterpene 17-hydroxy-kauran-3-one, has been achieved. The strategy is based on a diastereoselective oxidative polycyclization-pinacol tandem process consisting of transforming a functionalized phenol into a compact and complex tetracycle, which represents the main core of kaurane family members. The synthesis also includes an enantioselective Yamamoto's allylation, a diastereoselective Ru-catalyzed hydrocyanation, a ring-closing metathesis and a reductive isomerization process as key steps. The structure of our synthetic substrate was determined through comparison with an O-methylated derivative of the natural compound.

Graphical abstract: Asymmetric synthesis of (+)-17-epi-methoxy-kauran-3-one through tandem oxidative polycyclization-pinacol process

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Publication details

The article was received on 25 May 2016, accepted on 10 Jun 2016 and first published on 14 Jun 2016


Article type: Paper
DOI: 10.1039/C6OB01142J
Citation: Org. Biomol. Chem., 2016,14, 6744-6750
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    Asymmetric synthesis of (+)-17-epi-methoxy-kauran-3-one through tandem oxidative polycyclization-pinacol process

    G. Maertens, S. Desjardins and S. Canesi, Org. Biomol. Chem., 2016, 14, 6744
    DOI: 10.1039/C6OB01142J

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