Total Syntheses of the Isomeric Aglain Natural Products Foveoglin A and Perviridisin B: Selective Excited‐State Intramolecular Proton‐Transfer Photocycloaddition. (13th October 2017)

• Record Type: Journal Article
• Authors: Wang, Wenyu; Clay, Anthony; Krishnan, Retheesh; Lajkiewicz, Neil J.; Brown, Lauren E.; Sivaguru, Jayaraman; Porco, John A.
• Is Part Of: Angewandte Chemie. Volume 129:Number 46(2017)
• Page Start: 14671
• Page End: 14674
• Publication Date: 2017-10-13
• Subjects: Asymmetrische Synthesen -- Elektronentransfer -- Naturstoffe -- Photochemie -- Totalsynthesen; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201707539
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Selective excited‐state intramolecular proton‐transfer (ESIPT) photocycloaddition of 3‐hydroxyflavones with trans, trans ‐1, 4‐diphenyl‐1, 3‐butadiene is described. Using this methodology, total syntheses of the natural products (±)‐foveoglin A and (±)‐perviridisin B were accomplished. Enantioselective ESIPT photocycloaddition using TADDOLs as chiral hydrogen‐bonding additives provided access to (+)‐foveoglin A. Mechanistic studies have revealed the possibility for a photoinduced electron‐transfer (PET) pathway.