An angucycline antibiotic with a nonaromatic B ring, (+)-SF 2315A (3), was synthesized enantioselectively for the first time. A key transformation in the 23-step reaction sequence, which starts from (−)-quinic acid, is the stereocontrolled Diels-Alder reaction between diene 1 and bromojuglone 2. TIPS = triisopropylsilyl.
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Kim et al. (1995) studied this question.
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