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Winter, Nils; Trauner, Dirk (2017): Thiocarbonyl Ylide Chemistry Enables a Concise Synthesis of (+/-)-Hippolachnin A. In: Journal of the American Chemical Society, Vol. 139, No. 34: pp. 11706-11709
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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.