Skip to main content
SpringerLink
Log in

EPC synthesis of (+)-heptelidic acid

EPC-Synthese von (+)-heptelidsäure

  • Organische Cheme Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

An EPC (enantiomerically pure compound) synthesis of the antibiotic natural product (+)-heptelidic acid (1) is presented. Key step of the synthesis is a conjugate addition of the acetal protected vinyl cuprate4 to the auxiliary shielded enoate5n which gives the adduct7n as a single diastereomer. After cleavage of the acetal protecting group and of the chiral auxiliary the enantiomerically pure β-ketoester12 has been obtained which has been transformed to the title compound1 (11 steps starting from5n, 10.6% overall yield).

Zusammenfassung

Eine EPC-Synthese (EPC = enantiomerically pure compound) des antibiotischen Naturstoffes (+)-Heptelidsäure (1) wird präsentiert. Schlüsselschritt der Synthese ist dieMichael-Addition des acetal-geschützten Vinylcuprates4 an das auxiliargeschützte Enoat5n, wobei das Addukt7n in diastereomerenreiner Form erhalten wird. Nach der Abspaltung der Acetalschutzgruppe und des chiralen Auxiliars läßt sich der enantiomerenreine β-Ketoester12 herstellen, der in die Titelverbindung1 umgewandelt werden kann (11 Stufen ausgehend von5n, 10.6% Gesamtausbeute).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Hagenbach A (1971) Thesis. Eidgenössische Technische Hochschule, Zürich, Switzerland, Prom Nr 4674

  2. Arigoni D (1975) Pure and Appl Chem41: 219

    Google Scholar 

  3. Itoh Y, Kodama K, Furuya K, Takahashi S, Haneishi T, Takiguchi Y, Arai M (1980) J Antibiot33: 468

    Google Scholar 

  4. Itoh Y, Kodama K, Takahashi S, Haneishi T, Arai M (1980) J Antibiot33: 525

    Google Scholar 

  5. Stipanovic RD, Howell CR (1983) Tetrahedron39: 1103

    Google Scholar 

  6. Rohr M (1983) Thesis. Eidgenössische Technische Hochschule, Zürich, Switzerland, Prom Nr 5212

  7. Danishefsky SJ, Mantlo N (1988) J Am Chem Soc110: 8129

    Google Scholar 

  8. Sankyo Co, Jpn, Kokai Tokyo Koho 81 77281 (1981) Chem Abstr95: P185559s

  9. Mitsubishi Chemical Industries Co, Ltd, Jpn, Kokai Tokyo Koho 82 146793 (1983) Chem Abstr98: P70338p

  10. Endo A, Hasumi K, Sakai K, Kanbe T (1985) J Antibiot38: 920

    Google Scholar 

  11. Sakai K, Hasumi K, Endo A (1988) Biochim Biophys Acta952: 297

    Google Scholar 

  12. Sakai K, Hasumi K, Endo A (1991) Biochim Biophys Acta1077: 192

    Google Scholar 

  13. Austrian Fonds zur Förderung der wissenschaftlichen Forschung (Project number P11543-MED)

  14. Riehs G, Urban E (1996) Tetrahedron52: 1221

    Google Scholar 

  15. Riehs G, Urban E, Völlenkle H (1996) Tetrahedron52: 8725

    Google Scholar 

  16. Urban E, Riehs G, Knühl G (1995) Tetrahedron51: 11149

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Pharmaceutical Chemistry, University of Vienna, A-1090, Vienna, Austria

    G. Riehs & E. Urban

Authors
  1. G. Riehs
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. Urban
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Riehs, G., Urban, E. EPC synthesis of (+)-heptelidic acid. Monatsh Chem 128, 281–289 (1997). https://doi.org/10.1007/BF00807894

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00807894

Keywords

Search

Navigation