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Z-Ligustilide, a naturally occurring phthalide isolated from Ligusticum porteri, underwent Diels–Alder reactions with different dienophiles yielding novel tricyclic products with potentially interesting biological properties. Where selectivity was possible, the reactions performed showed regio- and stereoselectivity. The experimental results with ethyl acrylate were compared with the selectivity predicted...
The irradiation of the natural phthalide Z-ligustilide (1) gave the natural dimeric phthalide riligustilide (5), and three novel dimeric phthalides 7, 8 and 9. The chemo- and regio-selectivity involved in the formation of the photocyclodimers were analyzed by use of frontier molecular orbital methods and the preference in the formation of 7 was supported by the theoretical analysis.
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