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The first total synthesis of the potent and selective human blood coagulation factor XIa inhibitor clavatadine A (1) is described. Direct, early-stage guanidinylation enabled rapid, convergent access to an immediate clavatadine A precursor. Concomitant lactone hydrolysis and guanidine deprotection with aqueous acid cleanly provided clavatadine A (1) in only four steps (longest linear sequence, 41–43% overall yield).
Conn, S. J., Vreeland, S. M., Wexler, A. N., Pouwer, R. N., Quinn, R. J., & Chamberland, S. (2014). Total Synthesis of Clavatadine A. Journal of Natural Products, 78(1), 120–124. https://doi.org/10.1021/np500772u
Journal of Natural Products
Copyright © 2014 The American Chemical Society and American Society of Pharmacognosy
This article was originally published in Journal of Natural Products with an ACS AuthorChoice License. The full-text article from the publisher can be found here.