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Issue 12, 2012
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Fusarisetin A: scalable total synthesis and related studies

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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.

Graphical abstract: Fusarisetin A: scalable total synthesis and related studies

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Article information


Submitted
27 Jul 2012
Accepted
22 Aug 2012
First published
23 Aug 2012

Chem. Sci., 2012,3, 3378-3386
Article type
Edge Article

Fusarisetin A: scalable total synthesis and related studies

J. Xu, E. J. E. Caro-Diaz, M. H. Lacoske, Chao-I. Hung, C. Jamora and E. A. Theodorakis, Chem. Sci., 2012, 3, 3378
DOI: 10.1039/C2SC21308G

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