Furan Oxidation Reactions in the Total Synthesis of Natural Products

Abstract

Recent developments on the transformations of furans under oxidative conditions toward the total synthesis of complex natural compounds are discussed. Reactions and methods are classified according to the type of oxidant used. Comparisons are then made between all the strategies to provide a comprehensive overview. This review covers the most prominent work published from 2011 until 2017.1 Introduction2 Reagents and Methods for Oxidation of the Furan Ring2.1 Singlet Oxygen2.2 Peroxides and Hydroperoxides2.3 Quinones2.4 Halogen-Based Oxidants2.5 Chromium-Based Oxidants3 The Achmatowicz Reaction3.1 Halogen-Based Oxidants3.2 Hydroperoxides3.3 Enzymatic Oxidation4 Conclusion

Achmatowicz Rearrangement-Inspired Development of Green Chemistry, Organic Methodology, and Total Synthesis of Natural Products

“…The related aza-version of AchR was realized successfully to provide functionalized piperidinones/piperidines . Although AchR remains an effective method for de novo synthesis of various saccharides, the synthetic utility of (aza-)­AchR has been expanded greatly in the total synthesis of natural products, as summarized in four recent reviews by Ghosh et al, Mhaske et al, Trushkov et al, and Pattenden et al Scheme presents some selected examples of natural products achieved recently with (aza-)­AchR by other research groups (Ghosh et al, Zakarian et al, Srihari et al, Phillips et al, Prasad et al, O’Doherty et al, Padwa et al, Liebeskind et al, Qi et al, Takahashi et al, Li et al, and Carreira et al). In this Account, we will focus on our work on three aspects of AchR: green chemistry for AchR, novel transformations of AchR products, and an AchR-based synthetic strategy for the total synthesis of natural products.…”

Three-component approach to modular synthesis of tetra-substituted furans and pyrroles

“…Tetra-substituted furan and pyrrole units are two important classes of five-membered heterocycles. They are not only versatile building blocks 4 but also general skeletons widely found in bioactive natural products and pharmaceuticals, 5 such as pleurotin D; 6 galerucella pheromone; 7 atorvastatin, a medicine to treat high blood cholesterol and prevent heart disease; 8 and lamellarin K, a natural product exhibiting cytotoxicity and immunomodulatory activity (Scheme 1b). 9 While numerous methods including multicomponent reactions (MCRs) have been established for the synthesis of furans and pyrroles, 10 further development of novel methods to rapidly access densely functionalized and regio-defined tetra-substituted furans and pyrroles under metal-free conditions remains urgent.…”

Oxidative Ring-Opening Transformation of 5-Acyl-4-pyrones as an Approach for the Tunable Synthesis of Hydroxylated Pyrones and Furans

“…Pyrones and furans are important classes of oxygen-containing heterocyclic compounds that are widely distributed in nature, exhibit various beneficial biological activities (antitumor, antioxidant, antiviral, antifungal, and others), and are used in pharmaceuticals , and materials chemistry (Figure ). These heterocycles demonstrate a multifarious reactivity that made them convenient building blocks for the organic synthesis of complex molecules via various transformations, , including cycloadditions and ring-opening transformations . Also, it is important to note that hydroxylated 4-pyrones are widely used as chelating agents and fluorescent labels …”