One-Step Multigram-Scale Biomimetic Synthesis of Psiguadial B.
- Newton CG Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, 1015, Lausanne, Switzerland.
- Tran DN Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, 1015, Lausanne, Switzerland.
- Wodrich MD Laboratory for Computational Molecular Design, EPFL SB ISIC LCMD, BCH 5121, 1015, Lausanne, Switzerland.
- Cramer N Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, 1015, Lausanne, Switzerland.
- 2017-09-09
Published in:
- Angewandte Chemie (International ed. in English). - 2017
biomimetic synthesis
cyclization
natural products
terpenoids
total synthesis
Antineoplastic Agents
Benzaldehydes
Biomimetics
Chemistry Techniques, Synthetic
Cyclization
Hep G2 Cells
Humans
Indolequinones
Models, Molecular
Phloroglucinol
Polycyclic Sesquiterpenes
Sesquiterpenes
Stereoisomerism
Terpenes
English
A gram-scale synthesis of psiguadial B, a purported inhibitor of human hepatoma cell growth, has been achieved in one step by a biomimetic three-component coupling of caryophyllene, benzaldehyde, and diformylphloroglucinol. This cascade reaction is catalyzed by N,N'-dimethylethylenediamine, and proceeds at ambient temperature to generate four stereocenters, two rings, one C-O bond, and three C-C bonds. Combined computational and experimental investigations suggest the biosynthesis of the natural product is non-enzyme mediated, and is the result of a Michael addition between caryophyllene and a reactive ortho-quinone methide, followed by two sequential intramolecular cationic cyclization events.
- Language
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- English
- Open access status
- green
- Identifiers
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- DOI 10.1002/anie.201708333
- PMID 28884886
- Persistent URL
- https://folia.unifr.ch/global/documents/231326
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