Enantioselective Total Synthesis of Secalonic Acid E
Dhandapani Ganapathy1, Johannes R Reiner1, Lorenz E Löffler1
1Institute of Organic and Biomolecular Chemistry, Georg-August University of Göttingen, Tammannstrasse 2, 37077 Göttingen (Germany).
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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