De novo synthesis of dimerization-ready flavan unit via intramolecular Pummerer/Friedel–Crafts cascade

We describe the de novo synthesis of a dimerization-ready flavan derivative via the Pummerer/Friedel–Crafts cascade. This method allowed facile access to oligomeric proanthocyanidin natural products. The total synthesis of procyanidin B4 was achieved by this strategy.

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-09, Vol.20 (37), p.7419-7423
Main Authors: Betkekar, Vipul V., Suzuki, Keisuke, Ohmori, Ken
Format: Article
Language:English
Subjects:
Dimerization
Friedel-Crafts reaction
Natural products
Synthesis
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Description
Summary:We describe the de novo synthesis of a dimerization-ready flavan derivative via the Pummerer/Friedel–Crafts cascade. This method allowed facile access to oligomeric proanthocyanidin natural products. The total synthesis of procyanidin B4 was achieved by this strategy.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob01416e