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The interleukin-8 receptor antagonist frondosin B (1) was synthesized in 12 steps from commercially available 5-methoxysalicylaldehyde in a completely regiocontrolled manner. The key steps of the synthesis were a Friedel – Crafts reaction to form the 7-membered ring and a Diels – Alder reaction to build the 6-membered ring, thereby fixing the double bond in the proper position.
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Inoue et al. (2000) studied this question.
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