Synthesis of a Bicyclic Proline Analogue from l-Ascorbic Acid

Claudia Lalli; Andrea Trabocchi; Francesco Guarna; Claudia Mannino; Antonio Guarna

doi:10.1055/s-2006-942545

PAPER

Synthesis of a Bicyclic Proline Analogue from l-Ascorbic Acid

Claudia Lalli, Andrea Trabocchi*, Francesco Guarna, Claudia Mannino, Antonio Guarna
Dipartimento di Chimica Organica ‘Ugo Schiff’ and Laboratorio di Progettazione, Sintesi e Studio di Eterocicli Biologicamenti Attivi (HeteroBioLab), Università degli Studi di Firenze, Via della Lastruccia 13, 50019 Sesto Fiorentino (FI), Italy
Fax: +39(055)4573531; e-Mail: andrea.trabocchi@unifi.it;

Abstract

Alle Artikel dieser Rubrik

Abstract

The efficient synthesis of a bicyclic α-amino acid from l-ascorbic acid is presented. The synthetic procedure is a three-step process involving an S_N2 reaction of an amino acetal with an l-ascorbic acid derivative, followed by protection of the amine as a Fmoc urethane, and acid-promoted trans-acetalization to give the title compound. Inversion of the configuration at the stereocenter of the precursor derived from l-ascorbic acid allowed the formation of the corresponding bicyclic α-amino acid bearing the carboxylic group in the 2-exo configuration. Such Fmoc-protected α-amino acids can be considered as bicyclic mimetics of proline, and are particularly suited for solid-phase peptidomimetic chemistry.

Key words

scaffold - peptidomimetic - amino acids - peptides - proline

Volltext

Referenzen

References

1a Giannis A. Kolter T. Angew. Chem., Int. Ed. Engl. 1993, 32: 1244

1b Gante J. Angew. Chem., Int. Ed. Engl. 1994, 33: 1699

2 Trabocchi A. Guarna F. Guarna A. Curr. Org. Chem. 2005, 9: 1127

3 See for example: Hanessian S. McNaughton-Smith G. Lombart H.-G. Lubell WD. Tetrahedron 1997, 53: 12789

4a Damour D. Herman F. Labaudinière R. Pantel G. Vuilhorgne M. Mignani S. Tetrahedron 1999, 55: 10135

4b Wang Q. Tran Huu Dau M.-E. Sasaki NA. Potier P. Tetrahedron 2001, 57: 6455

4c Demange L. Cluzeau J. Ménez A. Dugave C. Tetrahedron Lett. 2001, 42: 651

4d Gorichko MV. Grygorenko OO. Komarov IV. Tetrahedron Lett. 2002, 43: 9411

4e Dahlgren A. Bråualt J. Kuaenström I. Nilsson I. Musil D. Samuelsson B. Bioorg. Med. Chem. 2002, 10: 1567

4f Wang XJ. Hart SA. Xu B. Mason MD. Goodell JR. Etzkorn FA. J. Org. Chem. 2003, 68: 2343

4g Donkor IO. Korukonda R. Huang TL. Le Cour L. Bioorg. Med. Chem. Lett. 2003, 13: 783

4h Jeannotte G. Lubell WD. J. Org. Chem. 2004, 69: 4656

4i Liu Y.-T. Wong JK. Tao M. Osterman R. Sannigrahi M. Girijavallabhan VM. Saksena AK. Tetrahedron Lett. 2004, 45: 6097

5a Kym K. Germanas JP. J. Org. Chem. 1997, 62: 2847

5b Halab L. Lubell WD. J. Org. Chem. 1999, 64: 3312

5c Halab L. Lubell WD. J. Am. Chem. Soc. 2002, 124: 2474

5d Chakraborty TK. Ghosh A. Kumar SK. Kunwar AC. J. Org. Chem. 2003, 68: 6459

5e Zhang W.-J. Berglund A. Kao JL.-F. Couty J.-P. Gershengorn MC. Marshall GR. J. Am. Chem. Soc. 2003, 125: 1221

5f Chierici S. Jourdan M. Figuet M. Dumy P. Org. Biomol. Chem. 2004, 2: 2437

6 For an account, see: Trabocchi A. Menchi G. Guarna F. Machetti F. Scarpi D. Guarna A. Synlett 2006, 331

7a Trabocchi A. Cini N. Menchi G. Guarna A. Tetrahedron Lett. 2003, 44: 3489

7b Trabocchi A. Menchi G. Rolla M. Machetti F. Bucelli I. Guarna A. Tetrahedron 2003, 59: 5251

7c Danieli E. Trabocchi A. Menchi G. Guarna A. Eur. J. Org. Chem. 2005, 4372

8 Wei CC. De Bernardo S. Tengi JP. Borgese J. Weigele M. J. Org. Chem. 1985, 50: 3462

9 Ermolenko L. Sasaki A. J. Org. Chem. 2006, 71: 693

10 Tanaka A. Yamashita K. Synthesis 1987, 570