Total syntheses of (Sp)-(+)- and (Rp)-(-)-spiniferin-1, a pair of unusual natural products with planar chirality |
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Authors: | Sun Yun-Shan Ding Kai Tian Wei-Sheng |
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Institution: | Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, China. |
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Abstract: | (S(p))-(+)-Spiniferin-1 and (R(p))-(-)-spiniferin-1, a pair of unusual marine natural products with planar chirality, were firstly synthesized via a polyfluoroalkanosulfonyl fluoride induced homoallylic carbocation rearrangement reaction. The chiral resolution and palladium-catalyzed β-H elimination of allylic alcohol derivatives were considered as the key steps of these divergent syntheses. |
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