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Synthesis 2023; 55(15): 2333-2342
DOI: 10.1055/a-2022-1809
paper
Special Issue dedicated to Prof. David A. Evans

Synthesis of the CDF Ring System of Hexacyclinic Acid

Alexandre Audic
,
Joëlle Prunet∗
The University of Glasgow is acknowledged for financial support. The Engineering and Physical Sciences Research Council (EPSRC) provided a doctoral training allocation to A.A. (EP/K503058/1).
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Abstract

Diverse approaches to prepare the nine-membered ring precursor of the DEF fragment of hexacyclinic acid are described, culminating in the synthesis of the CDF ring system of this natural product. The key steps are a Michael addition/elimination sequence and an original intramolecular Tsuji–Trost reaction of an enol with an allylic alcohol.

Key words

hexacyclinic acid - intramolecular Tsuji–Trost reaction - Crimmins aldol - relay ring-closing metathesis - natural products

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2022-1809.
  • Supporting Information


Publication History

Received: 18 November 2022

Accepted after revision: 30 January 2023

Accepted Manuscript online:
30 January 2023

Article published online:
02 March 2023

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  • References

  • 1 New address: A. Audic, Syneos Health, 2500 rue Einstein, Québec, QC, Canada.
  • 2 Höfs R, Walker M, Zeeck A. Angew. Chem. Int. Ed. 2000; 39: 3258
    CrossrefPubMed
  • 3 Kobayakawa Y, Mori Y, Okajima H, Terada Y, Nakada M. Org. Lett. 2012; 14: 2086
    CrossrefPubMed
    • 4a Stellfeld T, Bhatt U, Kalesse M. Org. Lett. 2004; 6: 3889
      CrossrefPubMed
    • 4b Stelmakh A, Stellfeld T, Kalesse M. Org. Lett. 2006; 8: 3485
      CrossrefPubMed
    • 4c Clarke PA, Cridland AP. Org. Lett. 2005; 7: 4221
      CrossrefPubMed
    • 4d Clarke PA, Cridland AP, Rolla GA, Iqbal M, Bainbridge NP, Whitwood AC, Wilson C. J. Org. Chem. 2009; 74: 7812
      CrossrefPubMed
    • 4e James P, Felpin F.-X, Landais Y, Schenk K. J. Org. Chem. 2005; 70: 7985
      CrossrefPubMed
    • 4f Toueg J, Prunet J. Org. Lett. 2008; 10: 45
      CrossrefPubMed
    • 4g Audic A, Oriez R, Prunet J. Tetrahedron 2021; 79: 131843
      Crossref
    • 5a Clarke PA, Grist M, Ebden M, Wilson C. Chem. Commun. 2003; 1560
      Crossref
    • 5b Clarke PA, Grist M, Ebden M, Wilson C, Blake AJ. Tetrahedron 2005; 61: 353
      Crossref
    • 5c Iqbal M, Black RJ. G, Winn J, Reeder AT, Blake AJ, Clarke PA. Org. Biomol. Chem. 2011; 9: 5062
      CrossrefPubMed
  • 6 Crimmins MT, Christie HM, Hughes CO. Org. Synth. 2011; 88: 364
    CrossrefPubMed
  • 7 Larsen MA, Hennessy ET, Deem MC, Lam Y.-h, Sauri J, Sather AC. J. Am. Chem. Soc. 2020; 142: 726
    CrossrefPubMed
  • 8 Crimmins MT, Knight JD, Williams PS, Zhang Y. Org. Lett. 2014; 16: 2458
    CrossrefPubMed
  • 9 Kowalski CJ, Weber AE, Fields KW. J. Org. Chem. 1982; 47: 5088
    CrossrefPubMed
  • 10 Liniger M, Neuhaus C, Hofmann T, Fransioli-Ignazio L, Jordi M, Drueckes P, Trappe J, Fabbro D, Altmann K.-H. ACS Med. Chem. Lett. 2011; 2: 22
    CrossrefPubMed
  • 11 Ito H, Takenaka Y, Fukunishi S, Iguchi K. Synthesis 2005; 3035
    Article in Thieme Connect
  • 12 Cornil J, Gonnard L, Bensoussan C, Serra-Muns A, Gnamm C, Commandeur C, Commandeur M, Reymond S, Guerinot A, Cossy J. Acc. Chem. Res. 2015; 48: 761
    CrossrefPubMed
  • 13 Aponick A, Li CY, Biannic B. Org. Lett. 2008; 10: 669
    CrossrefPubMed
  • 14 Kawai N, Lagrange J.-M, Uenishi J. Eur. J. Org. Chem. 2007; 2808
    Crossref
  • 15 Evans DA, Starr JT. J. Am. Chem. Soc. 2003; 125: 13531
    CrossrefPubMed
  • 16 Mathieson M. PhD Thesis. University of Glasgow; UK: 2014
    CrossrefGoogle Scholar
  • 17 Wasnaire P, de Merode T, Markó IE. Chem. Commun. 2007; 4755
    CrossrefPubMed