5-Ethyl-7-hydroxy-2,2-dimethyl-4 H -benzo[ d ][1,3]dioxin-4-one
PAPER
Total synthesis of the glycosylated macrolide antibiotic fidaxomicin
Org Lett 2015, 17(14): 3514
http://pubs.acs.org/doi/abs/10.1021/acs.orglett.5b01602
The first enantioselective total
synthesis of fidaxomicin, also known as tiacumicin B or lipiarmycin A3,
is reported. This novel glycosylated macrolide antibiotic is used in the
clinic for the treatment of Clostridium difficile infections.
Key features of the synthesis involve a rapid and high-yielding access
to the noviose, rhamnose, and orsellinic acid precursors; the first
example of a β-selective noviosylation; an effective Suzuki coupling of
highly functionalized substrates; and a ring-closing metathesis reaction
of a noviosylated dienoate precursor. Careful selection of protecting
groups allowed for a complete deprotection yielding totally synthetic
fidaxomicin.
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