Chronic Actinic Dermatitis to Sesquiterpene Lactones: [2+2] Photoreaction Toward Thymidine of (+) and (−) α-Methylene-Hexahydrobenzofuranone with a cis Ring Junction |
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Authors: | Sébastien Fuchs Valérie Berl Jean-Pierre Lepoittevin |
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Institution: | Laboratoire de Dermatochimie, Institut de Chimie, CNRS et Université de Strasbourg, Strasbourg, France. |
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Abstract: | (+) and (−) α-methylene-hexahydrobenzofuranone derivatives with a stereochemically pure cis ring junction were used as models of sesquiterpene lactones to study their photoreactivity toward thymidine. After 313 nm irradiation of a deoxygenated acetone solution of lactone models and thymidine, six 2+2] photoadducts were isolated for each enantiomer and fully characterized by a combination of NMR experiments. A common syn regioselectivity and exo stereoselectivity were observed for photoadducts. This high photoreactivity of α-methylene-γ-butyrolactone ring toward thymidine could be an explanation of the progressive evolution of allergic contact dermatitis toward chronic actinic dermatitis. |
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