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Synthesis of a Diels-Alder precursor for the Elisabethin A skeleton

A synthesis of a precursor 2 for the Elisabethin A skeleton is reported. Containing a masked quinone and a (E,Z)-diene sub-unit, it has the required elements for the envisaged intramolecular Diels-Alder reaction to form the tricyclic system of Elisabethin A. Starting from methylresorcinol, the sequence involves the preparation of an arylacetic acid, which was alpha-alkylated by a chiral building block. Subsequent HWE reaction and cis-selective Wittig olefination furnished the diene with the desired geometry.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H1849NO – PubChem