Publikation: Total Synthesis of (-)-Chokol A by an Asymmetric Domino Michael Addition-Dieckmann Cyclization
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2006
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Synlett. 2006, 2006(14), pp. 2223-2226. ISSN 0936-5214. eISSN 1437-2096. Available under: doi: 10.1055/s-2006-949653
Zusammenfassung
A convergent and asymmetric total synthesis of (-)-chokol A was accomplished in six steps starting from the α,β-unsaturated ester (E)-9 in an overall yield of 27% with an enantiomeric excess of 95%. The key step of this synthesis is the asymmetric tandem conjugate addition-Dieckmann cyclization of the higher-order cuprate 8 derived from vinyl bromide 7 with the α,β-unsaturated ester (E)-9.
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540 Chemie
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antifungal agents, asymmetric synthesis, Michael addition, tandem reaction, total synthesis
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GROTH, Ulrich, Christian KESENHEIMER, Paul KREYE, 2006. Total Synthesis of (-)-Chokol A by an Asymmetric Domino Michael Addition-Dieckmann Cyclization. In: Synlett. 2006, 2006(14), pp. 2223-2226. ISSN 0936-5214. eISSN 1437-2096. Available under: doi: 10.1055/s-2006-949653BibTex
@article{Groth2006Total-9742,
year={2006},
doi={10.1055/s-2006-949653},
title={Total Synthesis of (-)-Chokol A by an Asymmetric Domino Michael Addition-Dieckmann Cyclization},
number={14},
volume={2006},
issn={0936-5214},
journal={Synlett},
pages={2223--2226},
author={Groth, Ulrich and Kesenheimer, Christian and Kreye, Paul}
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<dcterms:abstract xml:lang="eng">A convergent and asymmetric total synthesis of (-)-chokol A was accomplished in six steps starting from the α,β-unsaturated ester (E)-9 in an overall yield of 27% with an enantiomeric excess of 95%. The key step of this synthesis is the asymmetric tandem conjugate addition-Dieckmann cyclization of the higher-order cuprate 8 derived from vinyl bromide 7 with the α,β-unsaturated ester (E)-9.</dcterms:abstract>
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