A Synthesis of the C1-C9 Fragment of Ionomycin Using Cationic η<sup>3</sup>-Allylicmolybdenum and -Iron Complexes

Cooksey, John; Kocienski, Philip; Li, Ying-Fa

doi:10.1135/cccc20051653

CCCC > Archive > 2005, Volume 70 > Issue 10 > p. 1653

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

John Cooksey^a, Philip Kocienski^a,* and Ying-Fa Li^b

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

Abstract

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.

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

Abstract

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