NMR Determination of the Absolute Configuration of a Macrophomate Synthase Inhibitor by Using an Axial Chiral Reagent

Hiroki FUKUI; Yukiharu FUKUSHI; Satoshi OHASHI; Hideaki OIKAWA; Satoshi TAHARA

doi:10.1271/bbb.65.1920

Organic Chemistry

NMR Determination of the Absolute Configuration of a Macrophomate Synthase Inhibitor by Using an Axial Chiral Reagent

Hiroki FUKUI, Yukiharu FUKUSHI, Satoshi OHASHI, Hideaki OIKAWA, Satoshi TAHARA

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Keywords: macrophomate synthase, absolute configuration, axially chiral reagent, MBCC, NOE

JOURNAL FREE ACCESS

2001 Volume 65 Issue 8 Pages 1920-1923

DOI https://doi.org/10.1271/bbb.65.1920

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Abstract

Macrophomate synthase catalyzes an extraordinary four-step transformation from oxalacetate and 2-pyrone to macrophomic acid by an intermolecular DielsAlder reaction. The absolute configuration of the most potent macrophomate synthase inhibitor; (−)-2-carboxylmethyl-1-methoxybicyclo[2.2.2]oct-5-ene-2-carboxylic acid, was determined to be (1S,2R,4R) by using an axial chiral reagent.

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