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Total Synthesis Of Clavatadine A, Stephanie J. Conn, Shannon M. Vreeland, Alexandra N. Wexler, Rebecca H. Pouwer, Ronald J. Quinn, Stephen Chamberland
Total Synthesis Of Clavatadine A, Stephanie J. Conn, Shannon M. Vreeland, Alexandra N. Wexler, Rebecca H. Pouwer, Ronald J. Quinn, Stephen Chamberland
All Faculty Scholarship for the College of the Sciences
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).