Verrica Pharmaceuticals Inc.

Aureogen Biosciences, Inc.

Auerogen Biosciences, Inc.

Peter Wuts

Ake P Elhammer

Steven R Schow

Matthew Gene Davidson

Brian Matthew Eklov

Brad Melvin Loertscher

The invention provides synthetic methods for the preparation of cantharidin and analogs thereof. In one aspect, the invention provides an improved Diels-Alder cycloaddition to generate a key intermediate en route to cantharidin and analogs thereof. In certain embodiments, the new Diels-Alder reaction involves reacting Compound (2) in the presence of furan, and in the absence of acid or increased pressure, in an aprotic polar solvent with slight warming, to yield Compound (1) in favorable yield and exo-endo ratio. In another aspect, the invention also provides a new Diels-Alder reaction between compounds of Formula (III) and furan to yield compounds of Formula (IV), which can then be transformed into cantharidin or analogs thereof. In yet another aspect, the invention describes a new palladium-mediated carbonylation providing another key intermediate en route to cantharidin and analogs thereof. In addition to synthetic methods, present invention also provides compounds (i.e., intermediates) useful in the synthesis of cantharidin and analogs thereof. Compounds provided herein may have biological activity, and therefore may be used in the treatment of diseases or conditions (e.g., infectious diseases and skin conditions).

Synthesis of cantharidin

In general, the invention relates to AbA derivatives that are useful for treating infection. These novel compounds are shown to be effective in treating various fungal infections. The invention also provides pharmaceutically acceptable compositions comprising said compounds and methods of using the compositions in the treatment of various fungal infections.

Aureobasidium derivatives and methods of synthesis

In general, the invention relates to methods of synthesizing AbA derivatives that are useful for treating infection and amenable to further chemical elaboration. These novel methods are scalable for industrial production and employ safer, simpler, and more efficient process conditions. Furthermore, the invention also provides novel compounds and intermediates useful for implementing the methods described herein and/or for the treatment of infection.

Aureobasidin derivatives and methods of synthesis

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Kalamazoo, MI, United States of America

Peter Wuts