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The synthesis of a thiophene-containing analogue of halenaquinone was realized. Key steps include an alkynyl ketone-benzocyclobutane Diels-Alder reaction to construct the C,D-ring naphthalene subunit, a Heck cyclization to form the quaternary carbon, and a ring closing metathesis to add the A-ring.

Citation

Bryan Wakefield, Robert J Halter, Peter Wipf. Synthesis of (+/-)-thiohalenaquinone by iterative metalations of thiophene. Organic letters. 2007 Aug 2;9(16):3121-4

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PMID: 17630756

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