<p>An electromediated oxidative coupling strategy for constructing spirodienone fragment has been developed and applied as the key step for the total synthesis of (±)-spirobroussonin B. This concise route was accomplished in only four steps, 41.6% overall yield and the key coupling reaction was demonstrated on a gram scale. The absolute configurations of the enantiomers were unambiguously determined by chiral resolution and ECD calculations. This work establishes a solid foundation for developing practical and efficient syntheses of spirobroussonin B and related analogues.</p> Graphical Abstract <p></p>

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First total synthesis of (±)-spirobroussonin B via electromediated oxidative coupling for constructing spirodienone ring

  • Hong-Ji Shi,
  • Xing-Ping Zhang,
  • Cong-Xi Gao,
  • Kun Xie,
  • Wu-Yan Chen,
  • Ming-Ming Li,
  • Kou Wang

摘要

An electromediated oxidative coupling strategy for constructing spirodienone fragment has been developed and applied as the key step for the total synthesis of (±)-spirobroussonin B. This concise route was accomplished in only four steps, 41.6% overall yield and the key coupling reaction was demonstrated on a gram scale. The absolute configurations of the enantiomers were unambiguously determined by chiral resolution and ECD calculations. This work establishes a solid foundation for developing practical and efficient syntheses of spirobroussonin B and related analogues.

Graphical Abstract