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A new and stereospecific synthesis for Conduritol-C 8 and Conduritol-E 13a has been developed starting from p-benzoquinone 1. 1,4-oxygen functionalities were introduced in both synthesis by the reduction of dibromo p-benzoquinone 2 with NaBH4. 2,3-oxygen functionalities were introduced by KMnO4 oxidation of 4 for Conduritol C 8. Oxidation of 3 with m-chloroperbenzoic acid gave 9. Acid-catalyzed ring opening reaction of 9 gave 10a which leads to Conduritol-E.
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Seçen et al. (1992) studied this question.
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