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Journal Article
Research Support, Non-U.S. Gov't
Thiocarbonyl Ylide Chemistry Enables a Concise Synthesis of (±)-Hippolachnin A.
Journal of the American Chemical Society 2017 August 31
Hippolachnin A (1) is an antifungal polyketide that bristles with ethyl groups mounted onto a caged heterotricyclic core. It has shown potent activity against Cryptococcus neoformans, a yeast that can affect immunocompromised patients as an opportunistic pathogen. Herein we describe a concise, diversifiable, and scalable synthesis of (±)-hippolachnin A (1). It features a powerful photochemical opening step, a diastereoselective addition of an ethyl cuprate and an unusual strategy to install two additional ethyl groups that makes use of a thiocarbonyl ylide generated in situ.
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