Synthesis of a C1-C11 fragment of Zincophorin using planar chiral, neutral π-allyl iron complexes.

A key step in the synthesis of a C1-C11 fragment of the ionophore antibiotic Zincophorin involves the addition of an α-alkoxyalkylcopper(I) reagent to a planar chiral, neutral π-allyl iron complex. The key allylic alkylation reaction is highly regio- and stereoselective with addition taking place at the γ-position anti to the metal centre.

A synthesis of an ionomycin calcium complex.

Caught in the middle: The ionomycin calcium complex (see structure; O red, Ca green) was the target of an approach featuring the efficient asymmetric synthesis of an allene by a copper(I)-mediated anti-selective S(N)2' reaction, a highly stereoselective gold(III)-catalyzed cycloisomerization of an alpha-hydroxyallene, and a Rh-catalyzed rearrangement of an alpha-diazo-beta-hydroxyketone.

Synthesis of the C1-C16 fragment of ionomycin using a neutral (eta3-allyl)iron complex.

Key steps in the synthesis of the C1-C16 polyketide fragment of ionomycin were the nucleophilic addition of an organocuprate to a neutral (eta3-allyl)iron complex and the construction of a beta-diketone moiety by the Rh-catalysed rearrangement of an alpha-diazo-beta-hydroxyketone.