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Synthesis of Chiloscyphones and the Biological Activities of Their Synthetic Intermediates Against Methicillin‐Resistant S taphylococcus aureus (MRSA)
Author(s) -
Shiina Junichi,
Obata Rika,
Tomoda Hiroshi,
Nishiyama Shigeru
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500928
Subject(s) - chemistry , moiety , ketone , total synthesis , staphylococcus aureus , imipenem , biological activity , stereochemistry , combinatorial chemistry , antibiotics , organic chemistry , biochemistry , bacteria , antibiotic resistance , in vitro , biology , genetics
The total syntheses of chiloscyphone ( 1 ) and isochiloscyphone ( 2 ) have been achieved. Furthermore, the synthetic intermediate 5 shows biological activity against methicillin‐resistant Staphyrococcus aureus , and compounds 5 , 17 , and 18 , display imipenem‐type activity. The tricyclic lactone framework, which includes an α,β‐unsaturated ketone moiety, might play a crucial role in the anti‐MRSA activity. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)