Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Thiocarbonyl Ylide Chemistry Enables a Concise Synthesis of (±)-Hippolachnin A

Thiocarbonyl Ylide Chemistry Enables a Concise Synthesis of (±)-Hippolachnin A
Dirk Trauner, Nils Winter
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.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b06815

DOI: 10.1021/jacs.7b06815

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