Collect. Czech. Chem. Commun. 2005, 70, 1653-1668

A Synthesis of the C1-C9 Fragment of Ionomycin Using Cationic η3-Allylicmolybdenum and -Iron Complexes

John Cookseya, Philip Kocienskia,* and Ying-Fa Lib

a School of Chemistry, Leeds University, Leeds LS2 9JT, U.K.
b Department of Chemistry, Glasgow University, Glasgow G12 8QQ, U.K.


A key step in the synthesis of the C1-C9 fragment of the ionophore antibiotic ionomycin involves the addition of an alkylcopper(I) reagent to an ester-functionalised cationic η3-allylicmolybdenum and an alkylzinc cuprate to the corresponding η3-allyliciron complex. The reaction is regioselective and the metal directs enantiofacial attack (anti). The stereochemistry of the reactions is proven by an independent synthesis.

Keywords: Ionophores; Antibiotics; π-Allyl complexes; Molybdenum; Iron; Cuprates; Total synthesis; Stereoselective alkylations.

References: 38 live references.