Premium
Enantioselective Total Synthesis of Secalonic Acid E
Author(s) -
Ganapathy Dhandapani,
Reiner Johannes R.,
Löffler Lorenz E.,
Ma Ling,
Gnanaprakasam Boopathy,
Niepötter Benedikt,
Koehne Ingo,
Tietze Lutz F.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503593
Subject(s) - enantioselective synthesis , stereocenter , stereochemistry , total synthesis , chemistry , sharpless asymmetric dihydroxylation , dihydroxylation , yield (engineering) , catalysis , organic chemistry , materials science , metallurgy
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.