Total synthesis of ionomycin using ring-opening strategies.
[structure: see text] The total synthesis of the polyether antibiotic ionomycin, a calcium ionophore, is described. The synthesis demonstrates the utility of ring-opening methodologies as applied to the synthesis of polypropionate and deoxypolypropionate subunits, which are found in two of the four fragments in the synthesis.
Lautens
Mark
M
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario M5S 3H6, Canada. mlautens@chem.utoronto.ca
Colucci
John T
JT
Hiebert
Sheldon
S
Smith
Nicholas D
ND
Bouchain
Giliane
G
D000447:Aldehydes / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D002118:Calcium / Q000737:chemistry; D006900:Hydroxylation; D007202:Indicators and Reagents; D015759:Ionomycin / Q000138:chemical synthesis*; D010126:Ozone / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D000900:Anti-Bacterial Agents; D007202:Indicators and Reagents; D015759:Ionomycin; D010126:Ozone; D002118:Calcium