First total synthesis of (±)-spirobroussonin B via electromediated oxidative coupling for constructing spirodienone
Hong-Ji Shi1, Xing-Ping Zhang1, Cong-Xi Gao1
1School of Pharmaceutical Science and Yunnan Key Laboratory of Pharmacology for Natural Products, Yunnan College of Modern Biomedical Industry, Kunming Medical University, Kunming, 650500, China.
None:
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.
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