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The dimeric metabolite acremine G was synthesized featuring a highly regioselective and stereoselective Diels-Alder reaction between a TBS-protected hydroquinone diene and a structurally related alkenyl quinone. The major endo [4 + 2] adduct slowly transforms to acremine G by the atmospheric air under the deprotection conditions (in situ generated HF).
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Arkoudis et al. (2009) studied this question.
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