title: Light-mediated total synthesis of 17-deoxyprovidencin.
abstract: An asymmetric synthesis of the diterpenoid 17-deoxyprovidencin is described. Key steps include an aldol addition, a base-catalyzed Wipf-type furan formation, a Z-selective ring-closing metathesis for macrocyclization, a photochemical E/Z isomerization to a highly strained and conformationally restricted ring system, and the stereoselective formation of two epoxides on the ring.
authors.affiliation: Universität Wien, Institute für Organische Chemie, Währinger Strasse 38, 1090 Wien (Austria).
authors.forename: Nina
authors.initials: N
authors.lastname: Toelle
authors.forename: Harald
authors.initials: H
authors.lastname: Weinstabl
authors.forename: Tanja
authors.initials: T
authors.lastname: Gaich
authors.forename: Johann
authors.initials: J
authors.lastname: Mulzer
mesh_terms: D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; C478991:providencin
keywords: furanocembranoids; macrocycles; metathesis; photoisomerization; total synthesis