SCHEDULED MAINTENANCE
Thermostable enzymes in organic synthesis, Part 6. Total synthesis of (S)–(–)-zearalenone using a TBADH-generated trifunctional chiron
Abstract
Chiral alcohols produced by Thermoanaerobium brockii alcohol dehydrogenase (TBADH)-catalysed asymmetric reduction of polyfunctional ketones are useful building blocks for natural products synthesis. In particular, the ability of TBADH to discriminate between two ketones having equal chemical reactivity is demonstrated by enzymatic reduction of dec-9-ene-2, 6-dione to produce optically pure (S)-2-hydroxydec-9-en-6-one. The total synthesis of (S)-(–)-zearalenone with optical purity that exceeds 99.5% has been achieved by using the latter compound as a starting material.
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