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

doi:10.1007/s13659-026-00630-2

Natural Products and Bioprospecting ›› 2026, Vol. 16 ›› Issue (5): 62-62.DOI: 10.1007/s13659-026-00630-2

• ORIGINAL ARTICLES • Previous Articles Next Articles

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

Hong-Ji Shi¹, Xing-Ping Zhang¹, Cong-Xi Gao¹, Kun Xie², Wu-Yan Chen¹, Ming-Ming Li², Kou Wang¹

1. School of Pharmaceutical Science and Yunnan Key Laboratory of Pharmacology for Natural Products, Yunnan College of Modern Biomedical Industry, Kunming Medical University, Kunming, 650500, China;
2. School of Ethnic Medicine, Yunnan University of Chinese Medicine, Kunming, 650500, China

Received:2025-12-24 Accepted:2026-03-17 Online:2026-10-08
Supported by:
This work was supported by the Reserve Talents Project for Yunnan Province Young and Middle-aged Academic and Technical Leaders (202205AC160073), Shanghai Municipal Commission of Science and Technology (23015821100), and Kunming Medical University Graduate Education Innovation Fund (2025S191) for partial financial support.

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

Hong-Ji Shi¹, Xing-Ping Zhang¹, Cong-Xi Gao¹, Kun Xie², Wu-Yan Chen¹, Ming-Ming Li², Kou Wang¹

1. School of Pharmaceutical Science and Yunnan Key Laboratory of Pharmacology for Natural Products, Yunnan College of Modern Biomedical Industry, Kunming Medical University, Kunming, 650500, China;
2. School of Ethnic Medicine, Yunnan University of Chinese Medicine, Kunming, 650500, China

通讯作者: Ming-Ming Li,E-mail:lmm_xiaobai@126.com;Kou Wang,E-mail:wangkou@kmmu.edu.cn
基金资助:
This work was supported by the Reserve Talents Project for Yunnan Province Young and Middle-aged Academic and Technical Leaders (202205AC160073), Shanghai Municipal Commission of Science and Technology (23015821100), and Kunming Medical University Graduate Education Innovation Fund (2025S191) for partial financial support.

Abstract

Abstract: 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.

Key words: Spirobroussonin B, Electromediated, 1,3-Diphenylpropane, Spirodienone fragment

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.

关键词: Spirobroussonin B, Electromediated, 1,3-Diphenylpropane, Spirodienone fragment

Hong-Ji Shi, Xing-Ping Zhang, Cong-Xi Gao, Kun Xie, Wu-Yan Chen, Ming-Ming Li, Kou Wang. First total synthesis of (±)-spirobroussonin B via electromediated oxidative coupling for constructing spirodienone ring[J]. Natural Products and Bioprospecting, 2026, 16(5): 62-62.

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

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

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