Work

Formation of Prenylated Pterocarpans from Synthetically Derived Demethylmedicarpin by Regioselective Gold(I)‐Catalyzed Intramolecular Hydroarylation and Related Reactions

Year: 2025

Type: article

Abstract: Three prenylated pterocarpans including erybraedin A and erybraedin C have been synthesized from (±)‐demethylmedicarpin, itself prepared in four simple steps starting from resorcinol and 2,4‐dimethoxyphenylacetic acid. A gold(I)‐catalyzed and two‐fold intramolecular hydroarylation (IMHA) reaction of a readily derived bis‐propargyl ether of (±)‐demethylmedicarpin proceeds with remarkable regioselectivity to afford the racemate of a recently reported but yet‐to‐be named bis‐2H‐chromene‐annulated pterocarpan‐containing natural product. A possible explanation for this potentially very useful selectivity is advanced. In a related reaction sequence, a readily derived bis‐allyl ether of (±)‐demethylmedicarpin undergoes a thermally‐induced and two‐fold aromatic Claisen rearrangement to give a 1:5 mixture of the racemic modifications of the isomeric and cytotoxic natural products erybraedin A and erybraedin C.

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.202500196

Authors: Bingyan Liu, Martin G. Banwell

Institutions: Jinan University, Guangdong Medical College

Language: English

Topic: Catalytic Alkyne Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: National Natural Science Foundation of China, Ministry of Science and Technology of the People's Republic of China

Awards: G3230607142, G7610507788, G8616210253