Synthesis of Stereochemical Library of a Potent Antimalarial Monocerin Derivative and Its Stereochemical Revision

This study presents a total synthesis and revision of the stereochemical configuration of a potent antimalarial lead compound 2 possessing a benzo-pyranone framework, which was derived from the (+)-monocerin natural product of marine fungi, Exserohilum sp. Chiral hypervalent iodine(III)-catalyzed oxylactonization and late-stage O-methylation were highlights of the synthesis, which enabled access to the library of all possible eight stereoisomers of 2 for further understanding of stereochemical structure activity relationships (S-SARs).