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

Winter, Nils und Trauner, Dirk (2017): Thiocarbonyl Ylide Chemistry Enables a Concise Synthesis of (+/-)-Hippolachnin A. In: Journal of the American Chemical Society, Bd. 139, Nr. 34: S. 11706-11709

Abstract

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.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 0002-7863
• Sprache: Englisch