Recent advances in Norrish–Yang cyclization and dicarbonyl photoredox reactions for natural product synthesis

• Peng-Xi Luo,
• Jin-Xuan Yang,
• Shao-Min Fu and
• Bo Liu

Beilstein J. Org. Chem. 2025, 21, 2315–2333, doi:10.3762/bjoc.21.177

• Peng-Xi Luo Jin-Xuan Yang Shao-Min Fu Bo Liu College of Chemistry, Sichuan University, 29 Wangjiang Rd., Chengdu, Sichuan 610064, China 10.3762/bjoc.21.177 Abstract In recent years, the Norrish–Yang cyclization and related photoredox reactions of dicarbonyls have been extensively utilized in

• natural product synthesis. This review summarizes the latest advancements in these reactions for constructing terpenoids, alkaloids, and antibiotics. Through Norrish–Yang cyclization, dicarbonyls (e.g., 1,2-diketones and α-keto amides) can efficiently construct sterically hindered ring structures, which

• synthesis of natural products but also establish a solid foundation for subsequent pharmaceutical investigations. Keywords: dicarbonyls; natural product; Norrish–Yang cyclization; photoredox; total synthesis; Introduction In the 1930s, Norrish documented the photodecomposition of aldehydes and ketones [1

Ring opening of photogenerated azetidinols as a strategy for the synthesis of aminodioxolanes

• Henning Maag,
• Daniel J. Lemcke and
• Johannes M. Wahl

Beilstein J. Org. Chem. 2024, 20, 1671–1676, doi:10.3762/bjoc.20.148

• . Key to the successful development of this two-step process is the identification of a benzhydryl-protecting group, which orchestrates the photochemical Norrish–Yang cyclization and facilitates the subsequent ring opening. Keywords: azetidine; Norrish–Yang cyclization; ring-opening reaction; ring

• by Norrish–Yang cyclization, which employs easily accessible α-aminoacetophenones as starting materials [11][12][13][14][15]. Furthermore, ring-opening reactions of azetidines have been recently achieved using sulfur and oxygen nucleophiles [16][17][18][19][20][21][22][23][24][25]. However, methods

• that target a combination of photochemical ring closure and subsequent functionalization are still underdeveloped [4][5][6][7]. Within this work, we describe our endeavours in identifying a suitable substrate to meet the photochemical requirements of the Norrish–Yang cyclization and allow for

Effects of anion complexation on the photoreactivity of bisureido- and bisthioureido-substituted dibenzobarrelene derivatives

• Heiko Ihmels and
• Jia Luo

Beilstein J. Org. Chem. 2011, 7, 278–289, doi:10.3762/bjoc.7.37

• resulting in regio- or stereoselective product formation. Indeed, this approach has been employed to carry out stereoselective photoreactions, for example [2 + 2] cycloaddition [4], [4 + 4] photocycloaddition [5], Norrish–Yang cyclization [6], and [6π] photocyclization [7]. Asymmetric photoreactions have