Synthesis 2019; 51(24): 4635-4644
DOI: 10.1055/s-0037-1610729
paper
© Georg Thieme Verlag Stuttgart · New York

Divergent Synthesis of Various 2-Aryl Iminocyclitols from (R)-p-Hydroxyphenylglycine

Vipin Kumar Jain
Weitere Informationen

Publikationsverlauf

Received: 05. Juli 2019

Accepted after revision: 02. September 2019

Publikationsdatum:
30. September 2019 (online)


Abstract

A concise and efficient synthesis of various 2-aryl iminocyclitols is reported from (R)-p-hydroxyphenylglycine using Upjohn dihydroxylation and base-promoted intramolecular cyclization. These 2-aryl iminocyclitols are the important structural framework of various bioactive compounds and also known as glycosidase inhibitors.

Supporting Information

 
  • References and Notes

    • 1a Butters TD, Dwek RA, Platt FM. Chem. Rev. 2000; 100: 4683
    • 1b Winchester B, Fleet GW. J. Glycobiology 1992; 2: 199
    • 1c Sears P, Wong C.-H. Angew. Chem. Int. Ed. 1999; 38: 2300
    • 1d Newman DJ, Cragg GM, Snader KM. Nat. Prod. Rep. 2000; 17: 215
    • 1e Jung M, Park M, Lee HC, Kang Y.-H, Kang ES, Kim SK. Curr. Med. Chem. 2006; 13: 1203
    • 1f Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond. Stütz AE. Wiley-VCH; Weinheim: 1998
    • 1g Compain P, Martin OR. Curr. Top. Med. Chem. 2003; 3: 541
    • 1h Zou W. Curr. Top. Med. Chem. 2005; 5: 1363
    • 1i Asano N, Nash RJ, Molyneux RJ, Fleet GW. J. Tetrahedron: Asymmetry 2000; 11: 1645
    • 2a Dwek RA, Butters TD, Platt FM, Zitzmann N. Nat. Rev. Drug Discovery 2002; 1: 65
    • 2b Tanaka Y, Kato J, Kohara M, Galinski MS. Antiviral Res. 2006; 72: 1
    • 2c Gerber-Lemaire S, Juillerat-Jeanneret L. Mini-Rev. Med. Chem. 2006; 6: 1043
    • 2d Fiaux H, Kuntz DA, Hoffman D, Janzer RC, Gerber-Lemaire S, Rose DR, Juillerat-Jeanneret L. Bioorg. Med. Chem. 2008; 16: 7337
    • 2e Chang C.-F, Ho C.-W, Wu C.-Y, Chao T.-A, Wong C.-H, Lin C.-H. Chem. Biol. 2004; 11: 1301
    • 2f Lee SM. Diabetes 1982; 31: 249
    • 2g Greimel P, Spreitz J, Stutz AE, Wrodnigg TM. Curr. Top. Med. Chem. 2003; 3: 513
    • 2h Asano N, Nishida M, Kato A, Kizu H, Matsui K, Shimada Y, Itoh T, Baba M, Watson AA, Nash RJ, Lilley PM. de Q, Watkin DJ, Fleet GW. J. J. Med. Chem. 1998; 41: 2565
    • 2i Robina I, Moreno-Vargas AJ, Carmona AT, Vogel P. Curr. Drug Metab. 2004; 5: 329
    • 2j Watson KA, Mitchell EP, Johnson LN, Son JC, Bichard CJ. F, Orchard MG, Fleet GW. J, Oikonomakos NG, Leonidas DD, Kontou M, Papageorgioui A. Biochemistry 1994; 33: 5745
    • 2k Watson AA, Fleet GW, Asano N, Molyneux RJ, Nash RJ. Phytochemistry 2001; 56: 265
    • 2l Bernacki RJ, Niedbala MJ, Korytnyk W. Cancer Metastasis Rev. 1985; 4: 81
    • 3a Matkhalikova SF, Malikov VM, Yunusov SY. Khim. Prir. Soedin. 1969; 5: 30 ; Chem. Abstr. 1969, 71, 132545z
    • 3b Iida H, Yamazaki N, Kibayashi C, Nagase K. Tetrahedron Lett. 1986; 27: 5393
    • 3c Matkhalikova SF, Malikov VM, Yunusov SY. Khim. Prir. Soedin. 1969; 5: 606 ; Chem. Abstr. 1970, 71, 25712d
  • 4 Khanov MT, Sultanov MB, Egorova MR. Farmakal. Alkaloidovserdech. Glikoyidov 1971; 210 ; Chem. Abstr. 1972, 77, 135091r
    • 5a Shibano M, Tsukamoto D, Masuda A, Tanaka Y, Kusano G. Chem. Pharm. Bull. 2001; 49: 1362
    • 5b Shibano M, Tsukamoto D, Kusano G. Heterocycles 2002; 57: 1539
    • 6a Tsou E.-L, Chen S.-Y, Yang M.-H, Wang S.-C, Cheng T.-RR, Cheng W.-C. Bioorg. Med. Chem. 2008; 16: 10198
    • 6b Liu C, Hou L, Meng A, Han G, Zhang W, Jiang S. Carbohydr. Res. 2016; 429: 135
    • 6c Lucas R, Balbuena P, Errey JC, Squire MA, Gurcha SS, Mcneil M, Besra GS, Davis BG. ChemBioChem 2008; 9: 2197
    • 6d Zhao H, Wang W.-B, Nakagawa S, Jia Y.-M, Hu X.-G, Fleet GW. J, Wilson FX, Nash RJ, Kato A, Yu C.-Y. Chin. Chem. Lett. 2013; 24: 1059
    • 6e Ramakrishna K, Jagadeesh Y, Ramakrishna KV. S, Rao JL, Rao BV. Eur. J. Org. Chem. 2016; 1693
    • 6f Li Y.-X, Iwaki R, Kato A, Jia Y.-M, Fleet GW. J, Zhao X, Xiao M, Yu C.-Y. Eur. J. Org. Chem. 2016; 1429
    • 6g Matsuura F, Hamada Y, Shioiri T. Tetrahedron Lett. 1994; 35: 733
    • 6h Dharuman S, Palanivel AK, Vankar YD. Org. Biomol. Chem. 2014; 12: 4983
    • 7a Uraguchi D, Nakamura S, Ooi T. Angew. Chem. Int. Ed. 2010; 49: 7562
    • 7b Kotland A, Accadbled F, Robeyns K, Behr J.-B. J. Org. Chem. 2011; 76: 4094
    • 7c Lingamurthy M, Jagadeesh Y, Ramakrishna K, Rao BV. J. Org. Chem. 2016; 81: 1367
    • 7d Yamaguchi M, Ikagaki D, Ueda H, Tokuyama H. J. Antibiot. 2016; 69: 253
    • 7e Kim J.-S, Kim G.-W, Kang J.-C, Myeong I.-S, Jung C, Lee Y.-T, Choo G.-H, Park S.-H, Lee G.-J, Ham W.-H. Tetrahedron: Asymmetry 2016; 27: 171
    • 7f Davies SG, Lee JA, Roberts PM, Thomson JE, West CJ. Tetrahedron 2012; 68: 4302
    • 7g Choi YJ, Kim YC, Park SJ, Jung JM, Kim YS, Kim IS, Jung YH. Tetrahedron 2017; 73: 4458
    • 7h Shankaraiah G, Kumar RS. C, Poornima B, Babu KS. Tetrahedron Lett. 2011; 52: 4885
    • 7i Jagadeesh Y, Rao BV. Tetrahedron Lett. 2011; 52: 6366
    • 7j Jagadeesh Y, Reddy JS, Rao BV, Swarnalatha JL. Tetrahedron 2010; 66: 1202
    • 7k Mallesham P, Vijaykumar BV. D, Shin D.-S, Chandrasekhar S. Tetrahedron Lett. 2011; 52: 6145
    • 7l Davies SG, Lee JA, Roberts PM, Thomson JE, West CJ. Tetrahedron Lett. 2011; 52: 6477
    • 7m Sato M, Gunji Y, Ikeno T, Yamada T. Synthesis 2004; 1434
    • 8a Chacko S, Ramapanicker R. J. Org. Chem. 2015; 80: 4776
    • 8b Chacko S, Kalita M, Ramapanicker R. Tetrahedron: Asymmetry 2015; 26: 623
    • 8c Petakamsetty R, Jain VK, Majhi PK, Ramapanicker R. Org. Biomol. Chem. 2015; 13: 8512
    • 8d Chacko S, Ramapanicker R. Tetrahedron Lett. 2015; 56: 2023
    • 8e Petakamsetty R, Das RP, Ramapanicker R. Tetrahedron 2014; 70: 9554
    • 8f Chacko S, Ramapanicker R. Eur. J. Org. Chem. 2012; 7120
    • 8g Philip AT, Chacko S, Ramapanicker R. Synthesis 2013; 45: 1997
    • 8h Philip AT, Chacko S, Ramapanicker R. J. Pept. Sci. 2015; 21: 887
    • 8i Chacko S, Ramapanicker R. ChemistrySelect 2016; 1: 4458
    • 8j Jain VK, Ramapanicker R. Tetrahedron 2017; 73: 1568
    • 8k Philip AT, Raju E, Ramapanicker R. Eur. J. Org. Chem. 2016; 5502
    • 8l Petakamsetty R, Ansari A, Ramapanicker R. Carbohydr. Res. 2016; 435: 37
  • 9 (R)-4-Hydroxyphenylglycine was first subjected to esterification followed by in situ Boc protection then phenolic O-methylation using K2CO3 and MeI. The ester was further reduced into an alcohol using LiAlH4 and later oxidized into an aldehyde using IBX. Wittig reaction of this aldehyde with Ph3P=CHCOOEt yielded olefin 6 in 59% yield overall.
    • 10a Karjalainen OK, Passiniemy M, Koskinen AM. P. Org. Lett. 2010; 12: 1145
    • 10b Van Rheenen V, Kelly RC, Cha DY. Tetrahedron Lett. 1976; 17: 1973
    • 10c Cha JK, Christ WG, Kishi Y. Tetrahedron Lett. 1983; 24: 3943