Synthesis 2013; 45(12): 1693-1700
DOI: 10.1055/s-0033-1338934
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-Muricatacin and a Formal Synthesis of CMI-977 from l-Malic Acid

Maria González
Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, 36310 Vigo, Spain   Fax: +34(986)812262   eMail: yagamare@uvigo.es   eMail: ggomez@uvigo.es
,
Zoila Gándara
Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, 36310 Vigo, Spain   Fax: +34(986)812262   eMail: yagamare@uvigo.es   eMail: ggomez@uvigo.es
,
Andrea Martínez
Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, 36310 Vigo, Spain   Fax: +34(986)812262   eMail: yagamare@uvigo.es   eMail: ggomez@uvigo.es
,
Generosa Gómez*
Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, 36310 Vigo, Spain   Fax: +34(986)812262   eMail: yagamare@uvigo.es   eMail: ggomez@uvigo.es
,
Yagamare Fall*
Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, 36310 Vigo, Spain   Fax: +34(986)812262   eMail: yagamare@uvigo.es   eMail: ggomez@uvigo.es
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 15. März 2013

Accepted after revision: 16. April 2013

Publikationsdatum:
08. Mai 2013 (online)


Abstract

A total synthesis of (+)-muricatacin and a formal synthesis of CMI-977 have been achieved using commercially available l-malic acid based on our furan approach to oxacyclic systems, the proven scope of which is thus broadened.

Supporting Information

 
  • References

    • 4a Canoa P, Vega N, Pérez M, Gómez G, Fall Y. Tetrahedron Lett. 2008; 49: 1149
    • 4b Kocienski PJ, Brown RC, Pommier A, Procter M, Schmidt B. J. Chem. Soc., Perkin Trans. 1 1998; 9
  • 5 For a synthesis of butenolide 17, see: Szlosek M, Franck X, Figadère B, Cave A. J. Org. Chem. 1998; 63: 5169
  • 7 Crystallographic data were collected on a Bruker Smart 1000 CCD diffractometer at CACTI (Universidade de Vigo) at 20 °C using graphite monochromated MoKα radiation (λ = 0.71073 Å), and were corrected for Lorentz and polarisation effects. The frames were integrated with the Bruker SAINT software package and the data were corrected for absorption using the program SADABS. The structures were solved by direct methods using the program SHELXS97. All non-hydrogen atoms were refined with anisotropic thermal parameters by full-matrix least-squares calculations on F2 using the program SHELXL97. Hydrogen atoms were inserted at calculated positions and constrained with isotropic thermal parameters. The structural data have been deposited with the Cambridge Crystallographic Data Centre (CCDC) with reference number CCDC 826376. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ [FAX: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk].
    • 8a Barton DH. R, Dorchak J, Jaszberenyl JC. Tetrahedron 1992; 48: 7435
    • 8b Barton DH. R, McCombie SW. J. Chem. Soc., Perkin Trans. 1 1975; 1574
  • 9 Zúñiga A, Pérez M, González M, Gómez G, Fall Y. Synthesis 2011; 3301
  • 10 Müller S, Liepold B, Roth GJ, Bestmann J. Synlett 1996; 521