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Enantioselective Total Synthesis and Structure Confirmation of the Natural Dimeric Tetrahydroxanthenone Dicerandrol C
Author(s) -
Ganapathy Dhandapani,
Reiner Johannes R.,
Valdomir Guillermo,
Senthilkumar Soundararasu,
Tietze Lutz F.
Publication year - 2017
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.201700020
Subject(s) - enantioselective synthesis , enantiopure drug , total synthesis , absolute configuration , stereochemistry , chemistry , enantiomer , palladium , skeleton (computer programming) , catalysis , organic chemistry , biology , anatomy
The first enantioselective total synthesis of natural dicerandrol C ( 1 c ) as its enantiomer containing a dimeric tetrahydroxanthenone skeleton is described starting from the enantiopure chromane 6 which was obtained through a Wacker‐type cyclization with >99 % ee . For the formation of the dimeric skeleton a palladium‐catalyzed Suzuki reaction was used. The synthesis allowed the confirmation of the absolute configuration of the dicerandrols.