Abstract
: Aflatoxins, which are produced by Aspergillus flavus, Aspergillus nomius, and Aspergillus parasiticus, are a group of pentacyclic natural products with difuran and coumarin skeletons. They mainly include aflatoxin B1, B2, G1, G2, M1, and M2. Biologically, aflatoxins are of concern to human health as they can be present as contaminants in food products. The unique skeletons of aflatoxins and their risk to human health have led to the publication of nine remarkable total syntheses (including three asymmetric syntheses) and ten formal total syntheses (including four asymmetric formal syntheses) of aflatoxins in the past 55 years. To better understand the mechanism of the biological activity of aflatoxins and their presence in samples from the food industry, this review summarizes progress in the total synthesis of aflatoxins.
Highlights
Aflatoxins (Figure 1) are a group of potent hepatocarcinogenic polyketide natural products produced by the fungi Aspergillus flavus and Aspergillus parasiticus (Groopman et al, 2008; Bräse et al, 2009; Wu, 2014)
The first total synthesis of (+)-aflatoxin B2 was achieved in 2.5% yield through eight linear steps
Having successfully assembled tricycle 20, the group turned toward the final stage of the total synthesis of aflatoxin B2: the Sc(OTf)3-promoted one-pot sequential reaction
Summary
Aflatoxins (Figure 1) are a group of potent hepatocarcinogenic polyketide natural products produced by the fungi Aspergillus flavus and Aspergillus parasiticus (Groopman et al, 2008; Bräse et al, 2009; Wu, 2014). Aflatoxins present a significant risk to human health as they can be present as contaminants in food products (Roze et al, 2013; Bashiry et al, 2021; Ismail et al, 2021; Mollayusefian et al, 2021). There is a need to obtain analytical samples from the food industry and understand the mechanism underlying the biological activity of aflatoxins. The mechanisms of the biological activities of many complex natural products, including aflatoxins, remain unknown due to the impracticality of isolating the products from their natural sources; the only alternative to obtaining the natural products is practical total synthesis. To better understand the effects of aflatoxins, this article reviews important developments in the organic total synthesis of aflatoxins during the past 55 years
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