Total synthesis of zincophorin and its methyl ester.
A total synthesis of the naturally occurring ionophore zincophorin has been realized. The route features an intramolecular oxymercuration of a cyclopropanemethanol and a Carroll-Claisen rearrangement for the respective elaboration of the C1-C12 and C13-C25 subunits, which have been assembled by using a highly diastereoselective titanium-mediated aldol condensation.
Defosseux
Magali
M
Laboratoire de Chimie Organique, asocié au CNRS, ESPCI, 10 rue Vauquelin 75231 Paris Cedex 05 - France.
Blanchard
Nicolas
N
Meyer
Christophe
C
Cossy
Janine
J
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000138:chemical synthesis*; D020650:Combinatorial Chemistry Techniques; D004952:Esters; D007202:Indicators and Reagents; D015394:Molecular Structure; D011422:Propionates; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D002264:Carboxylic Acids; D004952:Esters; D007202:Indicators and Reagents; D011422:Propionates; C488419:zincophorin methyl ester; C043279:zincophorin