A Concise, Enantioselective
Synthesis of (+)-Decarestrictine L from Tri-O-acetyl-d-glucal

Andrea Zúñiga; Manuel Pérez; Gonzalo Pazos; Generosa Gómez; Yagamare Fall

doi:10.1055/s-0029-1218774

PAPER

A Concise, Enantioselective Synthesis of (+)-Decarestrictine L from Tri-O-acetyl-d-glucal

Andrea Zúñiga, Manuel Pérez, Gonzalo Pazos, Generosa Gómez*, Yagamare Fall*
Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, 36310 Vigo, Spain
Fax: +34(986)812262; e-Mail: yagamare@uvigo.es; e-Mail: ggomez@uvigo.es;

Abstract

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Abstract

We describe a new and efficient approach to the enantioselective synthesis of (+)-(2R,3S,6R)-decarestrictine L from commercially available tri-O-acetyl-d-glucal, based on a stereoselective Michael addition.

Key words

Michael addition - Wolf-Kishner reaction - Wacker oxidation

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Referenzen

References

1 Grabley S. Hammann P. Huetter K. Kirsch R. Kluge H. Thiericke R. Mayer M. Zeeck A. J. Antibiot. 1992, 45: 1176

2a Göhrt A. Zeeck A. Hüetter K. Kirsch R. Kluge H. Thiericke R. J. Antibiot. 1992, 45: 66

2b Mayer M. Thiericke R. J. Antibiot. 1993, 46: 1372

3a Machinaga N. Kibayashi C. Tetrahedron Lett. 1993, 34: 5739

3b Clark JS. Whitlock GA. Tetrahedron Lett. 1994, 35: 6381

3c Nokami J. Taniguchi T. Ogawa Y. Chem. Lett. 1995, 43

3d Solladié G. Arce E. Bauder C. Carreño MC. J. Org. Chem. 1998, 63: 2332

3e Esumi T. Kimura R. Mori M. Iwabuchi Y. Irie H. Hatakeyama S. Heterocycles 2000, 52: 525

3f Lukesh JM. Donaldson WA. Tetrahedron: Asymmetry 2003, 14: 757

3g García I. Gómez G. Teijeira M. Terán C. Fall Y. Tetrahedron Lett. 2006, 47: 1333

3h Clark JS. Fessard TC. Whitlock GA. Tetrahedron 2006, 62: 73

4 For a recent review on biological and synthetic studies on the decarestrictine family during the last fifteen years, see: Riatto VB. Pilli RA. Victor MM. Tetrahedron 2008, 64: 2279

5

Although d-glucal is commercially available, tri-O-acetyl-d-glucal is much cheaper and can be used for large-scale synthesis.

6 Mori Y. Hayashi H. J. Org. Chem. 2001, 66: 8666

7a Hutchins RO. Milewski CA. Maryanoff BE. J. Am. Chem. Soc. 1973, 95: 3662

7b Davies MJ. Moody CJ. J. Chem. Soc., Perkin Trans. 1 1991, 1: 9

8 Marshall JA. Crooks SL. DeHoff BS. J. Org. Chem. 1988, 53: 1616

9a Tsuji J. Shiizu I. Yamamoto K. Tetrahedron Lett. 1976, 34: 2975

9b Clark JS. Fessard TC. Whitlock GA. Tetrahedron 2006, 62: 73

10 For our preliminary results of QSAR studies on decarestrictine L, see: García I. Munteanu CR. Fall Y. Gómez G. Uriarte E. Gonzalez-Diaz H. Bioorg. Med. Chem. 2009, 17: 165