Literature DB >> 25517413

Total synthesis of clavatadine A.

Stephanie J Conn1, Shannon M Vreeland, Alexandra N Wexler, Rebecca H Pouwer, Rebecca N Pouwer, Ronald J Quinn, Stephen Chamberland.   

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).

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Year:  2014        PMID: 25517413     DOI: 10.1021/np500772u

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.050


  2 in total

1.  Total Synthesis and Biological Evaluation of Clavatadines C-E.

Authors:  Kylee Maxfield; Morgan Payne; Stephen Chamberland
Journal:  ACS Omega       Date:  2022-06-22

2.  A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products.

Authors:  Christopher E Malmberg; Stephen Chamberland
Journal:  J Vis Exp       Date:  2016-09-09       Impact factor: 1.355

  2 in total

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