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Synthesis of 3-Oxaterpenoids and Its Application in the Total Synthesis of (±)-Moluccanic Acid Methyl Ester

Authors

  • Bin Li,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616 (Singapore)
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  • Yin-Chang Lai,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616 (Singapore)
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  • Dr. Yujun Zhao,

    1. Departments of Internal Medicine, University of Michigan, Ann Arbor, MI 48109 (USA)
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  • Yiu-Hang Wong,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616 (Singapore)
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  • Zhi-Liang Shen,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616 (Singapore)
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  • Prof. Teck-Peng Loh

    Corresponding author
    1. Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026 (China)
    2. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616 (Singapore)
    • Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026 (China)
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  • We thank Dr. Yong-Xin Li for X-ray analyses. We gratefully acknowledge the Nanyang Technological University and the Singapore Ministry of Education Academic Research Fund Tier 2 (MOE2010- T2-2-067 and MOE2011-T2-1-013) for financial support.

Abstract

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Cascades: An InBr3-catalyzed intermolecular polyene cyclization initiated by a Prins reaction provides a concise approach to 3-oxaterpenoid derivatives. The reaction is compatible with various aldehydes, ketones, and polyolefin–alcohol substrates. In addition, the total synthesis of (±)-moluccanic acid methyl ester was achieved in seven steps by using such a Prins–polyene cyclization as the key step.

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