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- W2100291242 abstract "Fusarisetin A (1) is a recently isolated natural product that displays an unprecedented chemical motif and remarkable bioactivities as a potent cancer migration inhibitor. We describe here our studies leading to an efficient and scalable total synthesis of 1. Essential to the strategy was the development of a new route for the formation of a trans-decalin moiety of this compound and the application of an oxidative radical cyclization (ORC) reaction that produces fusarisetin A (1) from equisetin (2) via a bio-inspired process. TEMPO-induced and metal/O2-promoted ORC reactions were evaluated. Biological screening in vitro confirms the reported potency of (+)-1. Importantly, ex vivo studies show that this compound is able to inhibit different types of cell migration. Moreover, the C5 epimer of (+)-1 was also identified as a potent cancer migration inhibitor, while (−)-1 and 2 were found to be significantly less potent. The optimized synthesis is applicable on gram scale and provides a solid platform for analogue synthesis and methodical biological study." @default.
- W2100291242 created "2016-06-24" @default.
- W2100291242 creator A5011497989 @default.
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- W2100291242 creator A5079996481 @default.
- W2100291242 creator A5081818198 @default.
- W2100291242 creator A5086202977 @default.
- W2100291242 date "2012-01-01" @default.
- W2100291242 modified "2023-10-07" @default.
- W2100291242 title "Fusarisetin A: scalable total synthesis and related studies" @default.
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