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Epoxide-Opening Cascades Triggered by a Nicholas Reaction: Total Synthesis of Teurilene

Authors

  • Julio Rodríguez-López,

    1. Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna, Francisco Sánchez, 2, 38206 La Laguna, Tenerife (Spain)
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  • Dr. Fernando Pinacho Crisóstomo,

    1. Instituto de Productos Naturales y Agrobiología, CSIC, Francisco Sánchez, 3, 38206 La Laguna, Tenerife (Spain)
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  • Dr. Nuria Ortega,

    1. Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna, Francisco Sánchez, 2, 38206 La Laguna, Tenerife (Spain)
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  • Prof. Matías López-Rodríguez,

    1. Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna, Francisco Sánchez, 2, 38206 La Laguna, Tenerife (Spain)
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  • Prof. Víctor S. Martín,

    Corresponding author
    1. Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna, Francisco Sánchez, 2, 38206 La Laguna, Tenerife (Spain)
    • Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna, Francisco Sánchez, 2, 38206 La Laguna, Tenerife (Spain)===

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  • Dr. Tomás Martín

    Corresponding author
    1. Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna, Francisco Sánchez, 2, 38206 La Laguna, Tenerife (Spain)
    2. Instituto de Productos Naturales y Agrobiología, CSIC, Francisco Sánchez, 3, 38206 La Laguna, Tenerife (Spain)
    • Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna, Francisco Sánchez, 2, 38206 La Laguna, Tenerife (Spain)===

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  • This research was supported by the Spanish MINECO, co-financed by ERDF (CTQ2011-28417-C02-01 and CTQ2011-22653). F.P.C. thanks the CSIC for a JAE postdoctoral contract, co-financed by FSE.

Abstract

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Natural inspiration: Based on the biosynthesis of squalene-derived polyethers, a total synthesis of teurilene is described. The carbocation formation in the Nicholas reaction serves to control the initiation of a polyepoxide ring-opening cascade. The three furan rings present in teurilene were obtained in excellent yield in one step. Boc=tert-butoxycarbonyl, TMS=trimethylsilyl.

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