Enantioselective Access to All-trans 5-Alkylpiperidine-3,4-diols: Application to
the Asymmetric Synthesis of the 1-N-Iminosugar
(+)-Isofagomine

Arnaud Rives; Yves Génisson; Vanessa Faugeroux; Nathalie Saffon; Michel Baltas

doi:10.1055/s-0029-1216935

PAPER

Enantioselective Access to All-trans 5-Alkylpiperidine-3,4-diols: Application to the Asymmetric Synthesis of the 1-N-Iminosugar (+)-Isofagomine

Arnaud Rives^a, Yves Génisson*^a, Vanessa Faugeroux^a, Nathalie Saffon^b, Michel Baltas^a
^a SPCMIB, UMR CNRS 5068, Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse Cedex 9, France
Fax: +(33)(5)61556011; e-Mail: genisson@chimie.ups-tlse.fr;
^b SFTCM, FR2599, Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse Cedex 9, France

Abstract

All articles of this category

Abstract

Access to 3,4-disubstituted N-benzylprolinol derivatives is described that, after optimization of the ring-enlargement reaction conditions, could be efficiently transformed into the corresponding 3-hydroxypiperidines. This approach was applied to the asymmetric synthesis of (+)-isofagomine relying on regio- and stereoselective oxirane opening with the cyanide anion of a pivotal epoxypyrrolidine.

Key words

iminosugar - piperidine - ring enlargement - epoxide opening

Full Text

References

<A NAME="RT05509SS-1">1</A> Asano N. Nash RJ. Molyneux RJ. Fleet GWJ. Tetrahedron: Asymmetry 2000, 11: 1645

<A NAME="RT05509SS-2A">2a</A> Asano N. Curr. Top. Med. Chem. 2003, 3: 471

<A NAME="RT05509SS-2B">2b</A> For a review on iminosugars as potential antiviral agents see: Greimel P. Spreitz J. Stutz AE. Wrodnigg TM. Curr. Top. Med. Chem. 2003, 3: 513

<A NAME="RT05509SS-2C">2c</A> For a review on iminosugars in anti-cancer therapy see: Wrodnigg TM. Steiner AJ. Ueberbacher BJ. Anti-Cancer Agents Med. Chem. 2008, 8: 77

<A NAME="RT05509SS-3A">3a</A> Miglitol and type 2 diabetes mellitus see: Scott LJ. Spencer CM. Drugs 2000, 59: 521

<A NAME="RT05509SS-3B">3b</A> Miglustat and Gaucher disease see: Lachman RH. Drugs Today 2006, 42: 29

<A NAME="RT05509SS-4">4</A> Norez C. Noel S. Wilke M. Bijvelds M. Jorna H. Melin P. DeJonge H. Becq F. FEBS Lett. 2006, 580: 2081

<A NAME="RT05509SS-5">5</A> For a review see: Ayad T. Génisson Y. Baltas M. Curr. Org. Chem. 2004, 8: 1211

<A NAME="RT05509SS-6A">6a</A> Ayad T. Génisson Y. Baltas M. Gorrichon L. Synlett 2001, 866

<A NAME="RT05509SS-6B">6b</A> Ayad T. Génisson Y. Baltas M. Gorrichon L. Chem. Commun. 2003, 582

<A NAME="RT05509SS-6C">6c</A> Ayad T. Génisson Y. Broussy S. Baltas M. Gorrichon L. Eur. J. Org. Chem. 2003, 2903

<A NAME="RT05509SS-6D">6d</A> Ayad T. Génisson Y. Baltas M. Org. Biomol. Chem. 2005, 3: 2626

<A NAME="RT05509SS-7">7</A> Rives A. Génisson Y. Faugeroux V. Zedde C. Lepetit C. Chauvin R. Saffon N. Andrieu-Abadie N. Colié S. Levade T. Baltas M. Eur. J. Org. Chem. 2009, 2474

<A NAME="RT05509SS-8">8</A> Part of this work has been published as a preliminary communication: Faugeroux V. Génisson Y. Andrieu-Abadie N. Colié S. Levade T. Baltas M. Org. Biomol. Chem. 2006, 4: 4437

<A NAME="RT05509SS-9A">9a</A> Fuson RC. Zirkle CL. J. Am. Chem. Soc. 1948, 70: 2760

<A NAME="RT05509SS-9B">9b</A> Paul R. Tchelitcheff S. Bull. Soc. Chim. Fr. 1958, 736

<A NAME="RT05509SS-9C">9c</A> Hammer CF. Heller SR. Craig JH. Tetrahedron 1972, 28: 239

<A NAME="RT05509SS-9D">9d</A> Hammer CF. Weber JD. Tetrahedron 1981, 37: 2173

<A NAME="RT05509SS-9E">9e</A> Harding KE. Burks SR. J. Org. Chem. 1984, 49: 40

<A NAME="RT05509SS-9F">9f</A> Calvez O. Chiaroni A. Langlois N. Tetrahedron Lett. 1998, 39: 9447

<A NAME="RT05509SS-9G">9g</A> Lee J. Hoang T. Lewis S. Weissman SA. Askin D. Volante RP. Reider PJ. Tetrahedron Lett. 2001, 42: 6223

<A NAME="RT05509SS-9H">9h</A> Deyine A. Deleroix J.-M. Langlois N. Heterocycles 2004, 64: 207

<A NAME="RT05509SS-9I">9i</A> Mino T. Saito A. Tanaka Y. Hasegawa S. Sato Y. Sakamoto M. Fujita T. J. Org. Chem. 2005, 70: 1937

<A NAME="RT05509SS-9J">9j</A> For a review see: Cossy J. Chem. Rec. 2005, 51: 70

<A NAME="RT05509SS-10A">10a</A> Cossy J. Dumas C. Michel P. Gomez Pardo D. Tetrahedron Lett. 1995, 36: 549

<A NAME="RT05509SS-10B">10b</A> Cossy J. Dumas C. Gomez Pardo D. Eur. J. Org. Chem. 1999, 1693

<A NAME="RT05509SS-11">11</A> Cossy J. Dumas C. Gomez Pardo D. Bioorg. Med. Chem. Lett. 1997, 7: 1343

<A NAME="RT05509SS-12">12</A> Cossy J. Dumas C. Gomez Pardo D. Synlett 1997, 905

<A NAME="RT05509SS-13">13</A> Cossy J. Mirguet O. Gomez Pardo D. Synlett 2001, 1575

<A NAME="RT05509SS-14">14</A> Déchamps I. Gomez Pardo D. Karoyan P. Cossy J. Synlett 2005, 1170

<A NAME="RT05509SS-15A">15a</A> Déchamps I. Gomez Pardo D. Cossy J. ARKIVOC 2007, (v): 38

<A NAME="RT05509SS-15B">15b</A> Déchamps I. Gomez Pardo D. Cossy J. Tetrahedron 2007, 63: 9082

<A NAME="RT05509SS-16A">16a</A> Wilken J. Kossenjans M. Saak W. Haase D. Pohl S. Martens J. Liebigs Ann./Recl. 1997, 573

<A NAME="RT05509SS-16B">16b</A> Mena M. Bonjosh J. Gomez Pardo D. Cossy J. J. Org. Chem. 2006, 71: 5930

<A NAME="RT05509SS-17A">17a</A> Cossy J. Mirguet O. Gomez Pardo D. Desmurs J.-R. Tetrahedron Lett. 2001, 42: 5705

<A NAME="RT05509SS-17B">17b</A> Cossy J. Mirguet O. Gomez Pardo D. Desmurs J.-R. Eur. J. Org. Chem. 2002, 3543

<A NAME="RT05509SS-18A">18a</A> Ouchi H. Mihara Y. Watanabe H. Takahata H. Tetrahedron Lett. 2004, 45: 7053

<A NAME="RT05509SS-18B">18b</A> Ouchi H. Mihara Y. Takahata H. J. Org. Chem. 2005, 70: 5207

<A NAME="RT05509SS-19A">19a</A> Jespersen TM. Dong W. Sierks MR. Skrydstrup T. Lundt I. Bols M. Angew. Chem., Int. Ed. Engl. 1994, 33: 1778

<A NAME="RT05509SS-19B">19b</A> Jespersen TM. Bols M. Sierks MR. Skrydstrup T. Tetrahedron 1994, 50: 13449

<A NAME="RT05509SS-20A">20a</A> Bols M. Acc. Chem. Res. 1998, 31: 1

<A NAME="RT05509SS-20B">20b</A> Lillelund VH. Jensen HH. Liang X. Bols M. Chem. Rev. 2002, 102: 515

<A NAME="RT05509SS-20C">20c</A> Zechel DL. Boraston AB. Gloster T. Boraston CM. Macdonald JM. Tilbrook DMG. Stick RV. Davies GJ. J. Am. Chem. Soc. 2003, 125: 14313

<A NAME="RT05509SS-21">21</A> Zhu X. Sheth KA. Li S. Chang H.-H. Fan J.-Q. Angew. Chem. Int. Ed. 2005, 44: 7450

<A NAME="RT05509SS-22A">22a</A> Yu Z. Sawkar AR. Whalen LJ. Wong C.-H. Kelly JW. J. Med. Chem. 2007, 50: 94

<A NAME="RT05509SS-22B">22b</A> Steet R. Chung S. Lee W.-S. Pine CW. Do H. Kornfeld S. Biochem. Pharmacol. 2007, 73: 1376

<A NAME="RT05509SS-23A">23a</A> Ichikawa Y. Igarashi Y. Ichikawa M. Suhara Y. J. Am. Chem. Soc. 1998, 120: 3007

<A NAME="RT05509SS-23B">23b</A> Kim YJ. Ichikawa M. Ichikawa Y. J. Org. Chem. 2000, 65: 2599

<A NAME="RT05509SS-23C">23c</A> Hansen SU. Bols M. J. Chem. Soc., Perkin Trans. 1 2000, 911

<A NAME="RT05509SS-23D">23d</A> Pandey G. Kapur M. Tetrahedron Lett. 2000, 41: 8821

<A NAME="RT05509SS-23E">23e</A> Pandey G. Kapur M. Synthesis 2001, 1263

<A NAME="RT05509SS-23F">23f</A> Zhao G. Deo UC. Ganem B. Org. Lett. 2001, 3: 201

<A NAME="RT05509SS-23G">23g</A> Best WM. Macdonald JM. Skelton BW. Stick RV. Matthew D. Tilbrook G. White AH. Can. J. Chem. 2002, 80: 857

<A NAME="RT05509SS-23H">23h</A> Guanti G. Riva R. Tetrahedron Lett. 2003, 44: 357

<A NAME="RT05509SS-23I">23i</A> Pandey G. Kapur M. Khan MI. Gaikwad SM. Org. Biomol. Chem. 2003, 1: 3321

<A NAME="RT05509SS-23J">23j</A> Liu HZ. Lillelund VH. Andersch J. Liang XF. Bols M. J. Carbohydr. Chem. 2004, 23: 223

<A NAME="RT05509SS-23K">23k</A> Banfi L. Guanti G. Paradivino M. Riva R. Org. Biomol. Chem. 2005, 3: 1729

<A NAME="RT05509SS-23L">23l</A> Meloncelli PJ. Stick RV. Aust. J. Chem. 2006, 59: 827

<A NAME="RT05509SS-23M">23m</A> Panfil I. Solecka J. Chmielewski M. J. Carbohydr. Chem. 2006, 25: 673

<A NAME="RT05509SS-23N">23n</A> Goddard-Borger ED. Stick RV. Aust. J. Chem. 2007, 60: 211

<A NAME="RT05509SS-23O">23o</A> Mihara Y. Ojima H. Imahori T. Yoshimura Y. Ouchi H. Takahata H. Heterocycles 2007, 72: 633

<A NAME="RT05509SS-23P">23p</A> Imahori T. Ojima H. Tateyama H. Mihara Y. Takahata H. Tetrahedron Lett. 2008, 49: 265

<A NAME="RT05509SS-23Q">23q</A> Imahori T. Ojima H. Yoshimura Y. Takahata H. Chem. Eur. J. 2008, 14: 10762

<A NAME="RT05509SS-23R">23r</A> Espeel PER. Piens K. Callewaert N. Van der Eycken J. Synlett 2008, 2321

<A NAME="RT05509SS-24">24</A> Caron M. Sharpless KB. J. Org. Chem. 1985, 50: 1557

<A NAME="RT05509SS-25">25</A> Konno H. Toshiro E. Hinoda N. Synthesis 2003, 2161

<A NAME="RT05509SS-26">26</A> Lakner FJ. Hager LP. J. Org. Chem. 1996, 61: 3923

<A NAME="RT05509SS-27">27</A> Ciaccio JA. Smrtka M. Maio WA. Rucando D. Tetrahedron Lett. 2004, 45: 7201

Crystal data for 12: C₁₄H₁₆N₂O, M = 228.29, orthorhombic, P2 (1)2 (1)2 (1), a = 4.8314 (4) Å, b = 9.9404 (8) Å, c = 25.912 (2) Å, α = β = γ = 90˚, V = 1244.44 (18) Å^³, Z = 4, ρ_calcd = 1.218 mg/m^³, F(000) = 488, λ = 0.71073 Å, T = 173 (2) K, crystal size 0.70 × 0.10 × 0.10 mm^³, 4458 reflections collected (2407 independent, R _int = 0.0408), R1 [I > 2σ(I)] = 0.0510, wR2 [all data] = 0.1115, largest diff. peak and hole: 0.202 and -0.164 e˙Å^-³. CCDC 722378 contains the supplementary crystallographic data for 12. It can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 (1223)336033; e-mail: deposit@ccdc.cam.ac.uk].

Crystal data for 16: C₁₅H₁₉NO₃, M = 261.31, monoclinic, P2 (1), a = 9.3250 (2) Å, b = 4.80970 (10) Å, c = 15.5678 (4) Å, α = γ = 90˚, β = 102.439 (2)˚, V = 681.83 (3) Å^³, Z = 2, ρ_calcd = 1.273 mg/m^³, F(000) = 280, λ = 0.71073 Å, T = 173 (2) K, crystal size 0.8 × 0.10 × 0.10 mm^³, 10163 reflections collected (3246 independent, R _int = 0.0214), R1 [I > 2σ(I)] = 0.0476, wR2 [all data] = 0.1289, largest diff. peak and hole: 0.252 and -0.172 e˙Å^-³. CCDC 722379 contains the supplementary crystallographic data for 16. It can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 (1223)336033; e-mail: deposit@ccdc.cam.ac.uk].

<A NAME="RT05509SS-30">30</A> Sheldrick GM. Acta Crystallogr., Sect. A 1990, 46: 467

SHELXL-97, Program for Crystal Structure Refinement: Sheldrick, G. M., University of Göttingen, 1997.