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Total Synthesis and Absolute Configuration Assignment of MRSA Active Garcinol and Isogarcinol
Author(s) -
Socolsky Cecilia,
Plietker Bernd
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.201406077
Subject(s) - absolute configuration , chemistry , total synthesis , enantiomer , stereochemistry , combinatorial chemistry
A short total synthesis of ( ± )‐garcinol and ( ± )‐isogarcinol, two endo ‐type B PPAPs with reported activity against methiciline resistant Staphylococcus aureus (MRSA), is presented. The separation of framework‐constructing from framework‐decorating steps and the application of two highly regio‐ and stereoselective Pd‐catalysed allylations, that is, the Pd‐catalysed decarboxylative Tsuji–Trost allylation and the diastereoselective Pd‐catalysed allyl–allyl cross‐coupling, are key elements that allowed the total synthesis to be accomplished within 13 steps starting from acetylacetone. After separation of the enantiomers the absolute configurations of the four natural products (i.e., (−)‐garcinol, (+)‐guttiferone E (i.e., ent ‐garcinol), (−)‐isogarcinol, and (+)‐isoxanthochymol (i.e., ent ‐isogarcinol)) were assigned based on ECD spectroscopy.