Synthesis 2019; 51(13): 2720-2728
DOI: 10.1055/s-0037-1611479
paper
© Georg Thieme Verlag Stuttgart · New York

A Short Synthesis of (2S,3S,4R)-Dihydroxyhomoprolines from d-Erythrose-Derived 5,6-Dihydro-2H-pyran-2-one

David S. Freitas
a   Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal   Email: mja@quimica.uminho.pt
,
Jennifer Noro
a   Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal   Email: mja@quimica.uminho.pt
,
a   Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal   Email: mja@quimica.uminho.pt
,
Mónica C. S. Fernandes
a   Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal   Email: mja@quimica.uminho.pt
,
António V. M. Baptista
a   Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal   Email: mja@quimica.uminho.pt
,
Joana F. C. Parente
a   Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal   Email: mja@quimica.uminho.pt
,
José E. Rodríguez-Borges
b   LAQV/REQUIMTE, Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, Portugal
,
António Gil Fortes
a   Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal   Email: mja@quimica.uminho.pt
,
Maria J. Alves*
a   Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal   Email: mja@quimica.uminho.pt
› Author Affiliations
Thanks are due to Fundação para a Ciência e a Tecnologia (FCT) for financial support to the research Unit LAQV/REQUIMTE (UID/QUI/50006/2013), FCT and FEDER (European Fund for Regional Development)-COMPETE-QREN-EU for financial support to CQ/UM, and to the NMR Portuguese network (PTNMR, Bruker Avance III 400-Univ. Minho).
Further Information

Publication History

Received: 13 February 2019

Accepted after revision: 19 March 2019

Publication Date:
15 April 2019 (online)


Abstract

(2S,3S,4R)-Dihydroxyhomoprolines were obtained from a six-carbon-atom lactone intermediate obtained from d-erythrose in a short synthesis, by facile operational methodology, in very good overall yields.

Supporting Information

 
  • References

  • 1 Taylor CM, Barker WD, Weir CA, Park JH. J. Org. Chem. 2002; 67: 4466
  • 2 Weir CA, Taylor CM. Org. Lett. 1999; 1: 787
  • 3 Baird PD, Dho JC, Fleet GW. J, Peach JM, Prout K, Smith PW. J. Chem. Soc., Perkin Trans. 1 1987; 1785
  • 4 Chirke SS, Rajender A, Lakshmi JK, Rao BV. Tetrahedron Lett. 2015; 56: 1218
  • 5 Fleet GW. J, Peach JM, Smith PW, Austin GN, Baird PD, Watkin DJ. Tetrahedron 1987; 43: 3095
  • 6 Gajare VS, Khobare SR, Datrika R, Reddy KS, Rajana N, Kumar S, Rao BV, Kumar UK. Tetrahedron Lett. 2015; 56: 6659
  • 7 Arakawa Y, Yoshifuji S. Chem. Pharm. Bull. 1991; 39: 2219
  • 8 Csatayov K, Davies SG, Figuccia AL. A, Fletcher AM, Ford JG, Lee JA, Roberts PM, Saward BG, Song H, Thomson JE. Tetrahedron 2015; 71: 9131
  • 9 Davies SG, Foster EM, Lee JA, Roberts PM, Thomson JE. Tetrahedron 2013; 69: 8680
  • 10 Sousa CE. A, Ribeiro AM. P, Gil Fortes A, Cerqueira NM. F. S. A, Alves MJ. J. Org. Chem. 2017; 82: 982
  • 11 Rocha JF, Freitas DS, Noro J, Silva Teixeira CS, Sousa CE. A, Alves MJ, Cerqueira NM. F. S. A. J. Org. Chem. 2018; 83: 8011
  • 12 Baker SR, Clissold DW, McKillop A. Tetrahedron Lett. 1988; 29: 991
  • 13 Zimmermann P, Schmidt RR. Liebigs Ann. Chem. 1988; 663
  • 14 Fengler-Veith M, Schwardt O, Kautz U, Krämer B, Jäger V. Org. Synth., Coll. Vol. X 2004; 405 ; Org. Synth. 2002, 78, 123
  • 15 Malle BM, Lundt I, Wrodnigg TM. Org. Biomol. Chem. 2008; 6: 1779
  • 16 Bock K, Lundt I, Pedersen C. Carbohydr. Res. 1979; 68: 313