Recent advances in Norrish–Yang cyclization and dicarbonyl photoredox reactions for natural product synthesis
Peng-Xi Luo, Jin-Xuan Yang, Shao-Min Fu, Bo Liu
TL;DR
This review highlights recent progress in using Norrish–Yang cyclization and dicarbonyl photoredox reactions to synthesize complex natural products.
Contribution
The paper provides a comprehensive overview of the latest applications and mechanisms of Norrish–Yang cyclization and quinone photoredox reactions in natural product synthesis.
Findings
Norrish–Yang cyclization efficiently constructs sterically hindered ring structures from dicarbonyls.
Quinone photoredox reactions enable stereoselective synthesis of structures like spiroketals via single-electron transfer.
These reactions offer streamlined pathways for assembling complex natural product frameworks.
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 can further undergo ring-opening or rearrangement reaction to assemble complex molecular frameworks. Additionally, quinone photoredox reactions involving single-electron transfer (SET) processes provide novel strategies for the stereoselective synthesis of useful structures such as spiroketals. This review, drawing on examples from recently reported natural product syntheses, elaborates on reaction mechanisms, factors governing regioselectivity and…
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Taxonomy
TopicsRadical Photochemical Reactions · Synthesis of Indole Derivatives · Photochromic and Fluorescence Chemistry