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Updated: Jun 11, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
A versatile synthesis of fumaquinone
Miguel Peña-López1, M Montserrat Martínez, Luis A Sarandeses
1Departamento de Química Fundamental, Universidade da Coruña, E-15071 A Coruña, Spain.
Abstract:
Fumaquinone, a novel prenylated naphthoquinone antibiotic, was synthetized from ethyl acetoacetate in three steps (58% overall yield). The key step of the synthesis is the construction of the naphthoquinone skeleton by a regioselective Diels-Alder reaction between a 2-alkyl 1,3-bis(trimethylsilyloxy)-1,3-diene derivative and a bromoquinone. This short and versatile approach confirms the structure of fumaquinone and allows the synthesis of derivatives at the C-6 position.
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