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Total Synthesis of (−)‐Lemonomycin
Author(s) -
Yoshida Atsushi,
Akaiwa Michinori,
Asakawa Tomohiro,
Hamashima Yoshitaka,
Yokoshima Satoshi,
Fukuyama Tohru,
Kan Toshiyuki
Publication year - 2012
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.201202073
Subject(s) - enterococcus faecium , total synthesis , enantioselective synthesis , chemistry , staphylococcus aureus , combinatorial chemistry , enterococcus , stereochemistry , organic chemistry , bacteria , antibiotics , catalysis , biology , biochemistry , genetics
When life gives you lemons : An efficient and convergent enantioselective total synthesis of (−)‐lemonomycin, which shows potent activity against methicillin‐resistant Staphylococcus aureus (MRSA) and vancomycin‐resistant Enterococcus faecium (VREF), is presented. The key reaction steps are a Hosomi–Sakurai‐type cyclization, a thermodynamically controlled Pictet–Spengler reaction, and a glycosidation reaction with lemonose (see scheme).
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