Enantioselective Total Synthesis of Secalonic Acid E |
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| Authors: | Dr Dhandapani Ganapathy Johannes R Reiner Lorenz E Löffler Dr Ling Ma Dr Boopathy Gnanaprakasam Benedikt Niepötter Ingo Koehne Prof?Dr Lutz F Tietze |
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| Institution: | 1. Institute of Organic and Biomolecular Chemistry, Georg‐August University of G?ttingen, Tammannstrasse 2, 37077 G?ttingen (Germany);2. Institute of Inorganic Chemistry, Georg‐August University of G?ttingen, Tammannstrasse 4, 37077 G?ttingen (Germany) |
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| Abstract: | The first enantioselective synthesis of a secalonic acid containing a dimeric tetrahydroxanthenone skeleton is described, using a Wacker‐type cyclization of a methoxyphenolic compound to form a chiral chroman with a quaternary carbon stereogenic center with >99 % ee. Further steps are a Sharpless dihydroxylation and a Dieckmann condensation to give a tetrahydroxanthenone. A late‐stage one‐pot palladium‐catalyzed Suzuki‐dimerization reaction leads to the 2,2′‐biphenol linkage to complete the enantioselective total synthesis of secalonic acid E in 18 steps with 8 % overall yield. |
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| Keywords: | enantioselective reactions palladium secalonic acids total synthesis Wacker oxidation xanthone |
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