Total Syntheses of the Isomeric Aglain Natural Products FoveoglinA and PerviridisinB: Selective Excited-State Intramolecular Proton-Transfer Photocycloaddition

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 (±)-foveoglinA and (±)-perviridisinB were accomplished. Enantioselective E...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-11, Vol.56 (46), p.14479
Main Authors: Wang, Wenyu, Clay, Anthony, Krishnan, Retheesh, Lajkiewicz, Neil J, Brown, Lauren E, Sivaguru, Jayaraman, Porco, John A
Format: Article
Language:English
Subjects:
1,3-Butadiene
Additives
Butadiene
Enantiomers
Hydrogen bonding
Natural products
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Summary: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 (±)-foveoglinA and (±)-perviridisinB were accomplished. Enantioselective ESIPT photocycloaddition using TADDOLs as chiral hydrogen-bonding additives provided access to (+)-foveoglinA. Mechanistic studies have revealed the possibility for a photoinduced electron-transfer (PET) pathway.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201707539