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Synthesis of ent-Nanolobatolide

Authors

  • Dr. Hau Man Cheng,

    1. Chemical Synthesis Laboratory@Biopolis, Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 11 Biopolis Way, The Helios Block, #03-08, Singapore 138667 (Singapore), Fax: (+65) 6874-5869
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  • Dr. Weiwei Tian,

    1. Chemical Synthesis Laboratory@Biopolis, Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 11 Biopolis Way, The Helios Block, #03-08, Singapore 138667 (Singapore), Fax: (+65) 6874-5869
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  • Dr. Philippe A. Peixoto,

    1. Chemical Synthesis Laboratory@Biopolis, Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 11 Biopolis Way, The Helios Block, #03-08, Singapore 138667 (Singapore), Fax: (+65) 6874-5869
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  • Dr. Bhartesh Dhudshia,

    1. Chemical Synthesis Laboratory@Biopolis, Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 11 Biopolis Way, The Helios Block, #03-08, Singapore 138667 (Singapore), Fax: (+65) 6874-5869
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  • Prof. Dr. David Y.-K. Chen

    Corresponding author
    1. Chemical Synthesis Laboratory@Biopolis, Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 11 Biopolis Way, The Helios Block, #03-08, Singapore 138667 (Singapore), Fax: (+65) 6874-5869
    • Chemical Synthesis Laboratory@Biopolis, Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 11 Biopolis Way, The Helios Block, #03-08, Singapore 138667 (Singapore), Fax: (+65) 6874-5869
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  • We thank Doris Tan (ICES) for assistance with high-resolution mass spectrometry (HRMS). Financial support for this work was provided by A*STAR, Singapore.

Abstract

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Efficient and adaptable: The key steps in the total synthesis of ent-nanolobatolide, the enantiomer of the novel and potent neuroprotective agent, involve an oxidative ring expansion of (−)-menthone, a Nazarov cyclization, an intermolecular Diels–Alder reaction, and an intramolecular epoxide-opening reaction (see scheme). The two latter transformations provided evidence in support of the speculated biosynthetic pathway.

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