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An efficient asymmetric synthesis of (–)-wodeshiol

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Abstract

An efficient synthesis of (–)-wodeshiol 1 is described. The key reactions include highly stereoselective aldol condensation of piperonal with the dianion of chiral oxazolidinone, subsequent intramolecular ring cyclization of the aldol product 8 and a diastereocontrolled oxygenation of dilactone 7 in good yield.

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Authors and Affiliations

  1. Department of Chemistry, Institute for Basic Sciences, College of Natural Sciences, Chungbuk National University, Cheongju, 361–763, Chungbuk, Korea

    SOON HO LEE

  2. Department of Neuroscience and Medical Research Institute, School of Medicine, Ewha Woman’s University, Seoul, 158–710, Korea

    JAE-CHUL JUNG

  3. Department of Herb Industry/Herb Resources Jungwon University, 85 Munmu-ro, Goesan-eup, Goesan-gun, Chungbuk, 367–805, Korea

    OEE SOOK PARK

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  1. SOON HO LEE
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  2. JAE-CHUL JUNG
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Correspondence to OEE SOOK PARK.

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LEE, S.H., JUNG, JC. & PARK, O.S. An efficient asymmetric synthesis of (–)-wodeshiol. J Chem Sci 123, 327–330 (2011). https://doi.org/10.1007/s12039-011-0078-3

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