Scalable Total Synthesis of (−)-Berkelic Acid by Using a Protecting-Group-Free Strategy

Authors

  • Prof. Dr. Francisco J. Fañanás,

    Corresponding author
    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Unidad Asociada al C.S.I.C., Universidad de Oviedo, Julián Clavería, 8, 33006 Oviedo (Spain)
    • Instituto Universitario de Química Organometálica “Enrique Moles”, Unidad Asociada al C.S.I.C., Universidad de Oviedo, Julián Clavería, 8, 33006 Oviedo (Spain)
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  • Dr. Abraham Mendoza,

    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Unidad Asociada al C.S.I.C., Universidad de Oviedo, Julián Clavería, 8, 33006 Oviedo (Spain)
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  • Tamara Arto,

    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Unidad Asociada al C.S.I.C., Universidad de Oviedo, Julián Clavería, 8, 33006 Oviedo (Spain)
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  • Dr. Baris Temelli,

    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Unidad Asociada al C.S.I.C., Universidad de Oviedo, Julián Clavería, 8, 33006 Oviedo (Spain)
    2. Permanent address: Hacettepe University, Department of Chemistry, 06800 Ankara (Turkey)
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  • Prof. Félix Rodríguez

    Corresponding author
    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Unidad Asociada al C.S.I.C., Universidad de Oviedo, Julián Clavería, 8, 33006 Oviedo (Spain)
    • Instituto Universitario de Química Organometálica “Enrique Moles”, Unidad Asociada al C.S.I.C., Universidad de Oviedo, Julián Clavería, 8, 33006 Oviedo (Spain)
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  • We gratefully acknowledge financial support from the MICINN of Spain (grant CTQ2010-16790), MEC (FPU-predoctoral grant to A.M.), FICYT of Principado de Asturias (Severo Ochoa predoctoral grant to T. A.), and TUBITAK-BIDEB Programme of Turkey (postdoctoral fellowship to B.T.). We also thank Prof. Dr. José Barluenga (Universidad de Oviedo-Spain) for his support.

Abstract

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Supply chain: The polycyclic core of (−)-berkelic acid (1) was constructed in just one step from very simple starting materials. The total synthesis of 1 involves a seven-step linear sequence. Protection/deprotection steps were avoided and all but the last step were performed on a gram scale. This synthesis could solve the supply problem associated with the exhaustion of the natural source.

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