Highly Diastereoselective 1,3-Dipolar
Cycloaddition of a d-Galactose-Derived Nitrone
with Dimethyl Maleate: Synthesis of Polyhydroxylated Perhydroaza­azulenes

Omprakash P. Bande; Vrushali H. Jadhav; Vedavati G. Puranik; Dilip D. Dhavale

doi:10.1055/s-0029-1217541

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synlett 2009(12): 1959-1963
DOI: 10.1055/s-0029-1217541

LETTER

Highly Diastereoselective 1,3-Dipolar Cycloaddition of a d-Galactose-Derived Nitrone with Dimethyl Maleate: Synthesis of Polyhydroxylated Perhydroazaazulenes

Omprakash P. Bande^a, Vrushali H. Jadhav^a, Vedavati G. Puranik^b, Dilip D. Dhavale*^a
^a Garware Research Centre, Department of Chemistry, University of Pune, Pune 411 007, India
Fax: +91(20)25691728; e-Mail: ddd@chem.unipune.ernet.in;
^b Center for Materials Characterization, National Chemical Laboratory, Pune 411 008, India

Further Information

Publication History

Received 26 February 2009
Publication Date:
03 July 2009 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

An intermolecular 1,3-dipolar cycloaddition of a d-galactose-derived nitrone with dimethyl maleate was found to be perfectly diastereoselective at the nitrone carbon to give exclusive formation of isoxazolidine. The N-O bond reductive cleavage in isoxazolidine followed by lactam reduction afforded a pyrrolidine ring skeleton with sugar appendage that on acetonide cleavage and reductive amino-cyclization gave hitherto unknown hydroxymethyl-substituted hexa- and pentahydroxy perhydroazaazulenes.

Key words

1,3-dipolar nitrone olefin cycloaddition (DNOC) - nitrone - iminosugars - inhibitors - diastereoselectivity

References and Notes

1a Pellissier H. Tetrahedron 2007, 63: 3235

Google Scholar
1b Ruck-Braun K. Tonia HE. Wierschem F. Chem. Soc. Rev. 2005, 34: 507

Google Scholar
1c Gothelf KV. Jorgensen KA. Chem. Rev. 1998, 98: 863

Google Scholar
1d Confalone PN. Huie EM. Org. React. 1988, 36: 1

Google Scholar
1e Torseel KBG. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis Feuer H. VCH; Weinheim: 1988.

Google Scholar
1f Ferrier RJ. Middleton S. Chem. Rev. 1993, 93: 2779

Google Scholar
1g Osborn HM. Gemmell N. Harwood LM. J. Chem Soc., Perkin Trans. 1 2002, 2419

Google Scholar
1h Frederickson M. Tetrahedron 1997, 53: 403

Google Scholar
1i Adams JP. Box DS. J. Chem. Soc., Perkin Trans. 1 1999, 749

Google Scholar
1j Karlsson S. Hogberg HE. Org. Prep. Proced. Int. 2001, 33: 103

Google Scholar
1k Koumbis AE. Gallos JK. Curr. Org. Chem. 2003, 7: 585

Google Scholar
1l STD#§l)Padwa A. Pearson WH. J. Nat. Prod. 2004, 67: 1074

Google Scholar
1m Padwa A. Pearson WH. Org. Process Res. Dev. 2004, 8: 293

Google Scholar
1n Padwa A. Pearson WH. J. Am. Chem. Soc. 2002, 124: 12633

Google Scholar
1o Cycloaddition Reactions in Organic Synthesis Vol. 8: Carruthers W. Tetrahedron Organic Chemistry Series, Pergamon Press; New York: 1990. p.269

Google Scholar
1p Advances in Cycloaddition Vol. 1: Curran DP. JAI Press; London: 1988.

Google Scholar
1q Advances in Cycloaddition Vol. 2: Curran DP. JAI Press; London: 1990.

Google Scholar
1r Advances in Cycloaddition Vol. 3: Curran DP. JAI Press; London: 1993.

Google Scholar
1s Gothelf KV. In Cycloaddition Reactions in Organic Synthesis Kobayashi S. Jorgensen KA. Wiley-VCH; Weinheim: 2002. Chap. 6. p.211

Google Scholar
1t Kanemasa S. In Cycloaddition Reactions in Organic Synthesis Kobayashi S. Jorgensen KA. Wiley-VCH; Weinheim: 2002. Chap. 7. p.249

Google Scholar
1u Kanemasa S. Nishiuchi M. Kamimura A. Hori K. J. Am. Chem. Soc. 1994, 116: 2324

Google Scholar
1v Singh R. Singh S. Bhella AK. Sexana M. Faruk AS. Ishar MPS. Tetrahedron 2007, 63: 2283

Google Scholar
1w Merino P. Tejero T. Laguna M. Cerrada E. Moreno A. Lopez JA. Org. Biomol. Chem. 2003, 1: 2336

Google Scholar
1x Kumar KRR. Mallesha H. Rangappa KS. Synth. Commun. 2003, 33: 1545

Google Scholar
1y Ding X. Taniguchi K. Ukaji Y. Inomata K. Chem. Lett. 2001, 5: 468

Google Scholar
1z Ooi H. Urushibara A. Esumi T. Iwabuchi Y. Hatakeyama S. Org. Lett. 2001, 3: 953

Google Scholar
(aa) Romeo G. Iannazzoa D. Pipernoa A. Romeoa R. Corsarob A. Rescifinab A. Chiacchio U. Mini-Rev. Org. Chem. 2005, 2: 59

Google Scholar
2a Merino P. Franco S. Merchan FL. Romero P. Tejero T. Uriel S. Tetrahedron: Asymmetry 2003, 14: 3731

Google Scholar
2b Torres-Sanchez MI. Borrachero P. Cabrera-Escribano F. Gomez-Guillen M. Angulo-Alvarez M. Álvarez E. Favre S. Vogel P. Tetrahedron: Asymmetry 2007, 18: 1809

Google Scholar
3a Karanjule NS. Markad SD. Sharma T. Sabharwal SG. Puranik VG. Dhavale DD. J. Org. Chem. 2005, 70: 1356

Google Scholar
3b Bande OP. Jadhav VH. Puranik VG. Dhavale DD. Tetrahedron: Asymmetry 2007, 18: 1176

Google Scholar
4a Elbein AD. Molyneux RJ. In Alkaloids: Chemical and Biological Perspectives Vol. 5.: Pelletier SW. Wiley-Interscience; New York: 1987.

Google Scholar
4b Howard AS. Michael JP. In The Alkaloids Vol. 28: Brossi A. Academic Press; New York: 1986. Chap. 3.

Google Scholar
4c Michael JP. Nat. Prod. Rep. 1990, 9: 485

Google Scholar
5a Zho H. Hans S. Cheng X. Mootoo DR. J. Org. Chem. 2001, 66: 1761

Google Scholar
5b Svansson L. Johnston BD. Gu J.-H. Patrik B. Pinto BM. J. Am. Chem. Soc. 2000, 122. 10769

Google Scholar
5c Izquiedro I. Plaza MT. Robles R. Mota AJ. Tetrahedron: Asymmetry 1998, 9: 1015

Google Scholar
5d Kang SH. Kim JS. Chem. Commun. 1998, 1353

Google Scholar
5e Kefalas P. Grierson DS. Tetrahedron Lett. 1993, 34: 3555

Google Scholar
5f Ina H. Kibayashi C. J. Org. Chem. 1993, 58: 52

Google Scholar
5g Burgess K. Chaplin DA. Henderson I. Pan YT. Elbein AD. J. Org. Chem. 1992, 57: 1103

Google Scholar
5h Furneaux RH. Mason JM. Tyler PC. Tetrahedron Lett. 1995, 36: 3055

Google Scholar
6a Truscheit E. Frommer W. Junge B. Muller L. Schmidt DD. Wingender W. Angew. Chem., Int. Ed. Engl. 1981, 20: 744

Google Scholar
6b Furneaux RH. Gainsford GJ. Mason JM. Tyler PC. Hartley O. Winchester BG. Tetrahedron 1997, 53: 245

Google Scholar
7 Humphries MJ. Matsumoto K. White SL. Olden K. Cancer Res. 1986, 46: 5215

Google Scholar
8a Karpas A. Fleet GWJ. Dwek RA. Petursson S. Namgoong SK. Ramsden NG. Jacob GS. Rademacher TW. Proc. Natl. Acad. Sci. U.S.A. 1988, 85: 9229

Google Scholar
8b Walker BD. Kowalski M. Goh WC. Kozarsky K. Krieger M. Rosen C. Rohrschneider L. Haseltine WA. Sodroski J. Proc. Natl. Acad. Sci. U.S.A. 1987, 84: 8120

Google Scholar
8c Sunkara PS. Bowling TL. Liu PS. Sjoerdsma A. Biochem. Biophys. Res. Commun. 1987, 148: 206

Google Scholar
9 Johnson HA. Thomas NR. Bioorg. Med. Chem. Lett. 2002, 12: 237

Crossref PubMed Google Scholar
10a Kajimoto T. Liu KKC. Pederson RL. Zhong Z. Ichikawa Y. Porco JA. Wong H. J. Am. Chem. Soc. 1991, 113: 6187

Google Scholar
10b Asano N. Kato A. Miyauchi M. Kizu H. Kameda Y. Watson AA. Nash RJ. Fleet GWJ. J. Nat. Prod. 1998, 61: 625

Google Scholar
10c Bols M. Lillelund VH. Jensen HH. Liang X. Chem. Rev. 2002, 102: 515 ; and references cited therein

Google Scholar
10d Stutz AE. Iminosugars as Glycosidase Inhibitors, Nojirimycin and Beyond Wiley-VCH; Weinheim: 1999.

Google Scholar
10e Heightman TD. Vasella AT. Angew. Chem. Int. Ed. 1999, 38: 750

Google Scholar
10f Jenson HH. Bols M. Acc. Chem. Res. 2006, 39: 259

Google Scholar
10g Ichikawa M. Igarashi Y. Ichikawa Y. Tetrahedron Lett. 1995, 36: 1767

Google Scholar
10h Pandey G. Kapur M. Khan MI. Gaikwad SM. Org. Biomol. Chem. 2003, 1: 3321

Google Scholar
10i Matin MM. Sharma T. Sabharwal SG. Dhavale DD. Org. Biomol. Chem. 2005, 3: 1702

Google Scholar
11 Vyavahare VP. Chakraborty C. Maity B. Chattopadhyay S. Puranik VG. Dhavale DD. J. Med. Chem. 2007, 50: 5519

Crossref Google Scholar
12a Markad SD. Karanjule NS. Sharma T. Sabharwal SG. Puranik VG. Dhavale DD. Org. Biomol. Chem. 2006, 4: 2549

Google Scholar
12b Torres-Sanchez MI. Borrachero P. Cabrera-Escribano F. Gomez-Guillen M. Angulo-Alvarez M. Dianez MJ. Estrada MD. Lopez-Castro A. Perez-Garrido S. Tetrahedron: Asymmetry 2005, 16: 3897

Google Scholar
12c Lindsay KB. Pyne SG. Tetrahedron 2004, 60: 4173

Google Scholar
12d Tremmel P. Geyer A. J. Am. Chem. Soc. 2002, 124: 8548

Google Scholar
12e Gavard O. Hersant Y. Alais J. Duverger V. Dilhas A. Bascou A. Bonnaffe D. Eur. J. Org. Chem. 2003, 3603

Google Scholar
12f Geyer A. Bockelmann D. Weissenbach K. Fischer H. Tetrahedron Lett. 1999, 40: 477

Google Scholar
12g Nath M. Mukhopadhyay R. Bhattacharjya A. Org. Lett. 2006, 8: 317

Google Scholar
13a Karanjule NS. Markad SD. Dhavale DD. J. Org. Chem. 2006, 71: 6273

Google Scholar
13b Dhavale DD. Markad SD. Karanjule NS. PrakashaReddy J. J. Org. Chem. 2004, 69: 4760

Google Scholar
13c Patil NT. Tilekar JN. Dhavale DD. J. Org. Chem. 2001, 66: 1065 ; and references cited therein

Google Scholar
14a Goti A. Cacciarini M. Cardona F. Brandi A. Tetrahedron Lett. 1999, 40: 2853

Google Scholar
14b Stafford JA. Tetrahedron Lett. 1995, 36: 681

Google Scholar
14c Denmark SE. Hurd AR. J. Org. Chem. 2000, 65: 2875

Google Scholar
14d Denmark SE. Seierstad M. Herbert B. J. Org. Chem. 1999, 64: 884

Google Scholar
14e Cicchi S. Marradi M. Vogel P. Goti A. J. Org. Chem. 2006, 71: 1614

Google Scholar
14f Closa M. Wightman RH. Synth. Commun. 1998, 28: 3443

Google Scholar
14g Yu Y., Ohno M., Eguchi S., Kawai T., Terada Y.; Tetrahedron; 1997, 53: 5413
14h Argyropoulos NG. Panagiotidis T. Coutouli-Argyropoulou E. Raptopoulou C. Tetrahedron 2007, 63: 321

Google Scholar
15 Dondoni A. Franco S. Junquera F. Merchan F. Merino P. Tejero T. Synth. Commun. 1994, 22: 2537

Google Scholar

16

The ^¹H NMR spectrum of crude compound obtained from evaporation of toluene, showed additional signals (<7%) corresponding to unreacted dimethyl maleate. However, no other signals corresponding to other diastereomers were detected.

17

All new compounds have been characterised by IR, ^¹H NMR, ^¹³C NMR, and elemental analysis. Selected Procedure and Analytical Data for Compound 5 A solution of nitrone 4 [¹4] (2.0 g, 5.5 mmol) and dimethyl maleate (2.3 g, 16.5 mmol) in toluene (20 mL) was stirred under nitrogen atmosphere at r.t. for 5 h. The reaction mixture was concentrated under reduced pressure and purified by column chromatography (n-hexane-EtOAc = 85:15) to afford cycloadduct as a white solid (2.5 g, 89%); mp 99-101 ˚C; R _f = 0.7 (hexane-EtOAc = 6:4); [α]_D ^²5 -83.5 (c 0.3, CHCl₃). IR (KBr): 1753, 1728, 1494
cm^-¹. ^¹H NMR (300 MHz, CDCl₃): δ = 1.22 (s, 3 H), 1.30 (s, 3 H), 1.35 (s, 3 H), 1.50 (s, 3 H), 3.62 (dd, J = 8.1, 1.5 Hz, 1 H), 3.96 (s, 3 H), 3.99 (s, 3 H), 3.93-4.30 (m, 2 H), 4.17 (d, J = 13.5 Hz, 1 H), 4.27 (dd, J = 4.8, 1.8 Hz, 1 H), 4.33 (dd, J = 7.8, 1.5 Hz, 1 H), 4.40 (d, J = 13.5 Hz, 1 H), 4.55 (dd, J = 7.8, 1.8 Hz, 1 H), 4.73 (d, J = 8.4 Hz, 1 H), 5.51 (d, J = 4.8 Hz, 1 H), 7.18-7.37 (m, 3 H) 7.38-7.47 (m, 2 H). ^¹³C NMR (75 MHz, CDCl₃): δ = 24.0, 24.8, 25.7, 26.1, 52.3, 52.4, 53.5, 61.9, 67.0, 67.5, 70.53, 70.59, 70.6, 78.9, 96.3, 108.4, 108.9, 127.0, 128.0 (s), 129.2 (s), 137.4, 169.4, 171.1. Anal. Calcd for C₂₅H₃₃NO₁₀: C, 59.16; H, 6.55. Found: C, 59.29; H, 6.42.
Analytical Data for Compound 6
Viscous oil; 85%. R _f = 0.5 (EtOAc); [α]_D ^²5 -69.77 (c 0.45, CHCl₃). IR (neat): 3540-3200, 1734, 1687, 1438 cm^-¹. ^¹H NMR (300 MHz, CDCl₃ + D₂O): δ = 1.20 (s, 3 H), 1.30 (s, 3 H), 1.40 (s, 3 H), 1.60 (s, 3 H), 3.45 (t, J = 5.7 Hz, 1 H), 3.63 (s, 3 H), 3.92-4.16 (m, 4 H), 4.28 (dd, J = 5.4, 2.1 Hz, 1 H), 4.37 (d, J = 5.7 Hz, 1 H), 4.53 (dd, J = 7.8, 2.1 Hz, 1 H), 5.21 (d, J = 15.6 Hz, 1 H), 5.56 (d, J = 5.4 Hz, 1 H), 7.10-7.40 (m, 5 H). ^¹³C NMR (75 MHz, CDCl₃): δ = 23.9, 24.5, 25.4, 26.1, 43.6, 47.1, 52.1, 57.4, 63.2, 70.2, 70.8, 70.9, 72.5, 96.4, 108.1, 109.2, 127.4, 127.5 (s), 128.6 (s), 134.9, 172.5, 172.7. Anal. Calcd for C₂₄H₃₁NO₉: C, 60.37; H, 6.54. Found: C, 60.25; H, 6.40. Analytical Data for Compound 7
White solid; 67%; mp 138-140 ˚C; R _f = 0.3 (EtOAc); [α]_D ^²5 -48.80 (c 0.25, CHCl₃). IR (KBr): 3600-3250, 1632, 1454 cm^-¹. ^¹H NMR (300 MHz, CDCl₃ + D₂O): δ = 1.38 (s, 6 H), 1.43 (s, 3 H), 1.46 (s, 3 H), 2.36 (dd, J = 9.9, 3.3 Hz, 1 H), 2.70-2.80 (m, 1 H), 2.82 (br d, J = 9.9, 1 H), 2.94 (t, J = 2.1 Hz, 1 H) 3.31 (t, J = 10.2 Hz, 1 H), 3.45 (d, J = 13.5 Hz, 1 H), 3.72 (dd, J = 10.2, 6.3 Hz, 1 H), 3.77 (d, J = 3.3 Hz, 1 H), 3.95 (br s, 1 H), 4.10 (d, J = 13.5 Hz, 1 H), 4.29-4.38 (m, 2 H), 4.64 (dd, J = 8.4, 2.4 Hz, 1 H), 5.64 (d, J = 5.1 Hz, 1 H), 7.15-7.40 (m, 5 H). ^¹³C NMR (75 MHz, CDCl₃): δ = 24.0, 24.9, 25.7, 26.2, 50.2, 58.5, 58.9, 64.5, 65.6, 67.3, 70.4, 71.0, 72.2, 72.9, 96.5, 108.6, 109.2, 126.7, 128.0 (s), 128.2 (s), 138.9. Anal. Calcd for C₂₃H₃₃NO₇: C, 63.43; H, 7.64. Found: C, 63.57; H, 7.79.
Analytical Data for Compound 8
Viscous oil; 80%; R _f = 0.4 (EtOAc); [α]_D ^²5 -63.76 (c 0.25, CHCl₃). IR (neat): 3600- 3200, 1687, 1415 cm^-¹. ^¹H NMR (300 MHz, CDCl₃ + D₂O): δ = 1.22 (s, 3 H), 1.28 (s, 3 H), 1.39 (s, 3 H), 1.44 (s, 3 H), 2.90 (t, J = 7.2 Hz, 1 H), 3.41 (t, J = 9.0 Hz, 1 H), 3.48-3.58 (m, 2 H), 3.63 (dd, J = 10.5, 6.6 Hz, 1 H), 3.97 (br s, 1 H), 4.03 (s, 1 H), 4.30 (dd, J = 4.8, 2.1 Hz, 1 H), 4.39 (d, J = 7.8 Hz, 1 H), 4.46 (s, 1 H), 4.60 (d, J = 7.8 Hz, 1 H), 5.07 (ABq, J = 12.6 Hz, 2 H), 5.54 (d, J = 4.8 Hz, 1 H), 7.18-7.40 (m, 5 H). ^¹³C NMR (75 MHz, CDCl₃): δ = 24.0, 25.0, 25.6, 25.7, 49.1, 55.0, 61.5, 63.3, 66.71, 66.78, 70.4, 70.8, 72.1, 72.2, 96.2, 109.3, 109.4, 127.5, 127.7 (s), 128.2 (s), 136.4, 155.3. Anal. Calcd for C₂₄H₃₁NO₉: C, 60.37; H, 6.54. Found: C, 60.59; H, 6.32.
Analytical Data for Compound 3a
Viscous oil; 80%; R _f = 0.25 (MeOH); [α]_D ^²5 +45.01 (c 0.25, MeOH). IR (neat): 3676-3250 cm^-¹. ^¹H NMR (300 MHz, D₂O): δ = 2.19 (m, 1 H), 2.81 (dd, J = 9.9, 2.7 Hz, 1 H), 3.13 (t, J = 9.0 Hz, 1 H), 3.27 (dd, J = 9.0, 6.9 Hz, 1 H), 3.61-3.78 (m, 2 H), 3.93 (dd, J = 9.9, 4.5 Hz, 1 H), 4.09 (d, J = 4.5 Hz, 1 H), 4.18-4.28 (m, 3 H), 4.94 (d, J = 6.0 Hz, 1 H). ^¹³C NMR (75 MHz, D₂O): δ = 53.8, 55.7, 60.1, 62.9, 66.9, 72.5, 75.6, 79.3, 84.6, 88.6. Anal. Calcd for C₁₀H₁₉NO₇: C, 45.29; H, 7.22. Found: C, 49.31; H, 7.30.
Analytical Data for Compound 3b
Viscous oil; 92%. R _f = 0.30 (MeOH). [α]_D ^²5 -3.0 (c 0.5, MeOH). IR (neat): 3670-3260 cm^-¹. ^¹H NMR (300 MHz, D₂O): δ = 2.51 (br d, J = 5.4 Hz, 1 H), 3.02 (br s, 1 H), 3.15 (br s 1 H), 3.35 (br s, 1 H), 3.53 (br d, J = 11.1 Hz, 1 H), 3.61 (dd, J = 11.7, 7.2 Hz, 1 H), 3.70-3.85 (m, 2 H), 3.86-4.06 (m, 2 H), 4.11 (d, J = 7.2 Hz, 1 H), 4.29 (br d, J = 5.4 Hz, 1 H), 4.39 (s, 1 H). ^¹³C NMR (75 MHz, D₂O): δ = 49.0, 55.3, 61.6 (s), 63.5, 66.8, 69.3, 71.3, 73.0, 74.2. Anal. Calcd for C₁₀H₁₉NO₆: C, 48.19; H, 7.68. Found: C, 48.30; H, 7.91.