During a recent synthesis of hispidospermidin, a fungal isolate and an inhibitor of

Chapter 20, Problem 20.93

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During a recent synthesis of hispidospermidin, a fungal isolate and an inhibitor of phospholipase C, the investigators employed a novel, aliphatic Friedel-Crafts acylation (J. Am. Chem. Soc. 1998, 120, 40394040). The following acid chloride was treated with a Lewis acid, affording two products in a 3:2 ratio. Propose a plausible mechanism for the formation of compounds 1 and 2. COCl H H AlCl3 O Cl + O 1 2

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