75306-38-6Relevant academic research and scientific papers
Thiocarbonyl Ylide Chemistry Enables a Concise Synthesis of (±)-Hippolachnin A
Winter, Nils,Trauner, Dirk
, p. 11706 - 11709 (2017)
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.
Synthesis and biological evaluation of (±)-hippolachnin and analogs
Winter, Nils,Rupcic, Zeljka,Stadler, Marc,Trauner, Dirk
, p. 375 - 383 (2019/04/26)
Due its unique structure and its reported potent antifungal activity, the marine polyketide hippolachnin A (1) has attracted much attention in the synthetic community. Herein, we describe the development of a concise, diversifiable and scalable synthesis of the racemic natural product, which serves as a platform for the generation of bioactive analogues. Biological testing of our synthetic material did not confirm the reported antifungal activity of hippolachnin A but unraveled moderate activity against nematodes and microbes.
