Synthesis of the Tetracyclic Framework of Polycyclic Spiro Lignan Natural Products | Zendy

Ghada Ali | Zendy; Gregory D. Cuny | Zendy

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Synthesis of the Tetracyclic Framework of Polycyclic Spiro Lignan Natural Products

Author(s) -

Ghada Ali,

Gregory D. Cuny

Publication year - 2020

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.0c00976

Subject(s) - lignan , fluorene , chemistry , friedel–crafts reaction , acylation , ring (chemistry) , ether , organic chemistry , stereochemistry , suzuki reaction , combinatorial chemistry , catalysis , palladium , polymer

Polycyclic spiro lignans are a new family of lignan natural products recently isolated from Gymnotheca involucrata . The first synthesis of two model substrates of this rare family of natural products was achieved in six steps. An efficient strategy that features Suzuki coupling and Friedel-Crafts acylation was employed to construct the ABC tricyclic fluorene framework. Subsequently, Grignard reaction followed by acid-mediated cyclization furnished the spiro cyclic ether ring D.

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