Total Synthesis of (-)-Chokol A by an Asymmetric Domino Michael Addition-Dieckmann Cyclization

Groth, Ulrich; Kesenheimer, Christian; Kreye, Paul

Total Synthesis of (-)-Chokol A by an Asymmetric Domino Michael Addition-Dieckmann Cyclization

Dateien

Total_Synthesis_of.pdfGröße: 93.61 KBDownloads: 1033

Datum

2006

Autor:innen

Groth, Ulrich

Kesenheimer, Christian

Kreye, Paul

Open Access-Veröffentlichung

Open Access Green

Sammlungen

Chemie

Publikationstyp

Zeitschriftenartikel

Publikationsstatus

Published

Erschienen in

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.

Fachgebiet (DDC)

540 Chemie

Schlagwörter

antifungal agents, asymmetric synthesis, Michael addition, tandem reaction, total synthesis

Zitieren

ISO 690

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-2006-949653

BibTex

@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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