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Direct Aldol Strategy in Enantioselective Total Synthesis of Thuggacin B
Author(s) -
Matsuzawa Akinobu,
Opie Christopher R.,
Kumagai Naoya,
Shibasaki Masakatsu
Publication year - 2014
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.201304297
Subject(s) - aldol reaction , stereocenter , enantioselective synthesis , total synthesis , stereochemistry , chirality (physics) , chemistry , catalysis , organic chemistry , physics , nambu–jona lasinio model , chiral symmetry breaking , quantum mechanics , quark
An enantioselective total synthesis of thuggacin B, a natural product exhibiting antibiotic activity against Mycobacterium tuberculosis, is described. Asymmetric direct aldol reactions promoted by Cu and Zn catalysts play a pivotal role in constructing four stereogenic centers. The use of direct aldol reactions as the initial steps for the synthesis of two key fragments allowed the construction of the other stereogenic centers through chirality transfer.