Total Synthesis of Clavatadine A

Authors

Stephanie J. Conn, Central Washington University
Shannon M. Vreeland, Central Washington University
Alexandra N. Wexler, Central Washington University
Rebecca H. Pouwer, Griffith University
Ronald J. Quinn, Griffith University
Stephen Chamberland, Central Washington University

Document Type

Article

Department or Administrative Unit

Chemistry

Publication Date

12-17-2014

Abstract

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).

Comments

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.

Recommended Citation

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

Journal of Natural Products

Rights

Copyright © 2014 The American Chemical Society and American Society of Pharmacognosy