Laboratoire de Dermatochimie, Institut de Chimie, CNRS et Université de Strasbourg, Strasbourg, France.
Photochem Photobiol. 2010 May-Jun;86(3):545-52. doi: 10.1111/j.1751-1097.2009.00691.x. Epub 2010 Jan 22.
(+) and (-) alpha-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 alpha-methylene-gamma-butyrolactone ring toward thymidine could be an explanation of the progressive evolution of allergic contact dermatitis toward chronic actinic dermatitis.
(+)和(-)α-亚甲基-六氢苯并呋喃酮衍生物具有立体化学纯的顺式环连接，被用作倍半萜内酯的模型，以研究它们对胸腺嘧啶的光反应性。在 313nm 照射下，将内酯模型和胸腺嘧啶的脱氧丙酮溶液进行照射，从每个对映异构体中分离出六种[2+2]光加合物，并通过 NMR 实验的组合进行了充分的表征。观察到光加合物具有共同的顺区域选择性和外立体选择性。α-亚甲基-γ-丁内酯环对胸腺嘧啶的这种高光反应性可以解释过敏性接触性皮炎向慢性光化性皮炎的逐渐演变。
