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Asymmetric synthesis of machilin C and its analogue

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Abstract

Full details of the asymmetric total synthesis of erythro-8-O-4′-neolignan, machilin C, and its analogue perseal A are reported. The synthesis was involved in the Sharpless dihydroxylation reaction that occurred with excellent asymmetric induction, and the Mitsunobu reaction which occurred with inversion of the absolute configuration from the threo to the erythro isomer. The synthesis was achieved from simple vanillin in eight to twelve steps.

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Authors and Affiliations

  1. College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao, 266042, China

    Yamu Xia & Wei Wang

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  1. Yamu Xia
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  2. Wei Wang
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Correspondence to Yamu Xia.

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Xia, Y., Wang, W. Asymmetric synthesis of machilin C and its analogue. Chem. Pap. 64, 630–636 (2010). https://doi.org/10.2478/s11696-010-0040-8

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  • DOI: https://doi.org/10.2478/s11696-010-0040-8

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