Total Syntheses of the Isomeric Aglain Natural Products Foveoglin A and Perviridisin B: Selective Excited‐State Intramolecular Proton‐Transfer Photocycloaddition | Zendy

Wang Wenyu | Zendy; Clay Anthony | Zendy; Krishnan Retheesh | Zendy; Lajkiewicz Neil J. | Zendy; Brown Lauren E. | Zendy; Sivaguru Jayaraman | Zendy; Porco John A. | Zendy

Premium

Total Syntheses of the Isomeric Aglain Natural Products Foveoglin A and Perviridisin B: Selective Excited‐State Intramolecular Proton‐Transfer Photocycloaddition

Author(s) -

Wang Wenyu,

Clay Anthony,

Krishnan Retheesh,

Lajkiewicz Neil J.,

Brown Lauren E.,

Sivaguru Jayaraman,

Porco John A.

Publication year - 2017

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201707539

Subject(s) - intramolecular force , chemistry , excited state , proton , hydrogen bond , photochemistry , stereochemistry , molecule , organic chemistry , atomic physics , physics , quantum mechanics

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research