Novel biomimetic Schenck-ene/Hock/aldol tandem rearrangement reaction and its application in natural product synthesis and scaffold editing
Peer-Reviewed Publication
Updates every hour. Last Updated: 1-Jan-2026 06:11 ET (1-Jan-2026 11:11 GMT/UTC)
The Jingjing Wu group at the National Key Laboratory of Synergistic Materials Creation/Frontier Science Center for Transformative Molecules (FSCTM) at Shanghai Jiao Tong University, in collaboration with the Xiaosong Xue group at the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, recently reported a novel biomimetic Schenck-ene/Hock/aldol tandem rearrangement reaction mediated by singlet oxygen and its synthetic applications. Using this tandem reaction, they synthesized four natural products, alstoscholarinoid A, masterpenoid D, leontogenin, and marsformoxide B, in a clustered, one- to four-step process from readily available, inexpensive naturally resourced molecules. The mild reaction conditions and high functional group tolerance suggest that this strategy could serve as a novel approach for molecular backbone editing of natural products. Computational chemistry studies further revealed the mechanistic details of the rearrangement reaction and the factors that control the different rearrangement pathways of the key intermediate hydroperoxide. This study, published in CCS Chemistry, provides new insights into the synthesis of related natural products and molecular backbone editing and reconstruction
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