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Construction of 3,6-Anhydrohexosides via Intramolecular Cyclization of Triflates and Its Application to the Synthesis of Natural Product Isolated from Leaves of Sauropus rostratus

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posted on 03.10.2014, 00:00 by Long Liu, Cheng-Qian Wang, Dan Liu, Wei-Gang He, Jin-Yi Xu, Ai-Jun Lin, He-Quan Yao, Genzoh Tanabe, Osamu Muraoka, Wei-Jia Xie, Xiao-Ming Wu
A novel synthetic approach to construct various 3,6-anhydrohexosides via an intramolecular cyclization of corresponding triflates is described. The nucleophilic attack from C3 p-methoxybenzylated hydroxyl to C6 trifluoromethanesulfonate on triflate structures triggered the cyclization reaction to provide 3,6-anhydrohexosides in excellent yields, making the strategy more efficient with respect to the reported protocols. By applying this methodology, a concise first total synthesis of natural product isolated from leaves of Sauropus rostratus was accomplished.