Skip to main content
SpringerLink
Log in

A Lemieux–Johnson oxidation of shikimic acid derivatives: facile entry to small library of protected (2S,3S,4R)-2,3,4,7-tetrahydroxy-6-oxoheptanals

  • Original Paper
  • Published:
Chemical Papers Aims and scope Submit manuscript

Abstract

The Lemieux–Johnson oxidation was employed for the cleavage of the carbon–carbon double bond of shikimic acid derivatives. Through this procedure, a series of the sixteen novel (2S,3S,4R)-2,3,4,7-tetrahydroxy-6-oxoheptanals bearing three contiguous stereocentres have been synthesized in excellent yields.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Scheme 3

Similar content being viewed by others

References

  • Alves C, Barros T, Maycock CD, Ventura MR (1999) An efficient transformation of quinic acid to shikimic acid derivatives. Tetrahedron 55:8443–8456. doi:10.1007/s12272-012-1010-1

    Article  CAS  Google Scholar 

  • Blanco B, Prado V, Lence E et al (2013) Mycobacterium tuberculosis shikimate kinase inhibitors: design and simulation studies of the catalytic turnover. J Am Chem Soc 135(33):12366–12376. doi:10.1021/ja405853p

    Article  CAS  Google Scholar 

  • Bochkov DV, Sysolyatin SV, Kalashnikov AI, Surmacheva IA (2012) Shikimic acid: review of its analytical, isolation, and purification techniques from plant and microbial sources. J Chem Biol 5(1):5–17. doi:10.1007/s12154-011-0064-8

    Article  Google Scholar 

  • Cuelar MA, Quinones N, Vera V, Salas CO, Estevez JC, Estevez RJ (2015) Preliminary studies on the synthesis of (−)-shikimic acid based 1,2,3,4-tetrahydrobenzo[b]phenanthridine-7,12-diones. Synlett 26:552–556. doi:10.1055/s-005-28645

    Article  Google Scholar 

  • Díaz M, Ferrero M, Fernández S, Gotor V (2000) 6-s-cis Locked analogues of the steroid hormone 1-alpha, 25-dihydroxyvitamin D(3). Synthesis of novel A-ring stereoisomeric 1, 25-dihydroxy-3-epi-19-nor-previtamin D(3) derivatives. J Org Chem 65(18):5647–5652

    Article  Google Scholar 

  • Estévez AM, Estévez RJ (2012) A short overview on the medicinal chemistry of (−)-shikimic acid. Mini Rev Med Chem 12(14):1443–1454. doi:10.18520/v109/i9/1672-1679

    Article  Google Scholar 

  • Ghosh S, Chisti Y, Banerjee UC (2012) Production of shikimic acid. Biotechnol Adv 30(6):1425–1431. doi:10.1016/j.biotechadv.2012.03.001

    Article  CAS  Google Scholar 

  • González-Castro MA, Poole DL, Estévez JC, Fleet GWJ, Estévez RJ (2015) A stereoselective transformation of (−)-shikimic acid into (3R,4S,5R,7R)-7- hydroxymethyl)azepane-3,4,5-triol, a potential glycosidase inhibitor. Tetrahedron Asymmetry 26:320–323. doi:10.1016/j.tetasy.2015.02.005

    Article  Google Scholar 

  • Grewe R, Jensen H, Schnoor M (1956) Darstellung und Eigenschaften des Shikimialkohols. Chem Ber 89:898–901. doi:10.1002/cber.19560890412

    Article  CAS  Google Scholar 

  • Liu A, Liu ZZ, Zou ZM, Chen SZ, Xu LZ, Yang SL (2004) Synthesis of (+)-zeylenone from shikimic acid. Tetrahedron 60:3689–3694. doi:10.1248/cpb.54.1459

    Article  CAS  Google Scholar 

  • Magano J (2009) Synthetic approaches to the neuraminidase inhibitors Zanamivir (Relenza) and oseltamivir phosphate (Tamiflu) for the Treatment of influenza. Chem Rev 109(9):4398–4438. doi:10.1021/cr800449m

    Article  CAS  Google Scholar 

  • Pappo R, Allen DS Jr, Lemieux RU, Johnson WS (1956) Osmium tetroxide-catalyzed periodate oxidation of olefinic bonds. J Org Chem 21(4):478–479. doi:10.1021/jo01110a606

    Article  CAS  Google Scholar 

  • Quan N, Nie LD, Zhu RH, Shi XX, Ding W, Lu X (2013) Total syntheses of (+)-valiolamine and (−)-1-epi-valiolamine from naturally abundant (−)-shikimic acid. Eur J Org Chem 78:6389–6396. doi:10.1002/ejoc.201300804

    Article  Google Scholar 

  • Rawat G, Tripathi P, Saxena RK (2013) Expanding horizons of shikimic acid. Recent progresses in production and its endless frontiers in application andmarket trends. Appl Microbiol Biotechnol 97(10):4277–4287. doi:10.1007/s00253-013-4840-y

    Article  CAS  Google Scholar 

  • Sanchez-Abella L, Fernández S, Armesto N, Ferrero M, Gotor V (2006) Novel and efficient syntheses of (−)-methyl 4-epi-shikimate and 4,5-epoxyquinic and shikimic acid derivatives as key precursors to prepare new analogues. J Org Chem 71:5396–5399. doi:10.1021/jo0606249

    Article  CAS  Google Scholar 

  • Zhang Y, Liu A, Ye ZG, Lin J, Xu LZ, Yang SL (2006) New approach to the total synthesis of (Pharmacokinet)-zeylenone from shikimic acid. Chem Pharm Bull (Tokyo) 54:1459–1461. doi:10.1248/cpb.54.1459

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The present work was supported by the Grant Agency (Grant No. 1/0398/14) of the Ministry of Education, Slovak Republic. It was also supported by the Slovak Research and Development Agency (Grant No. APVV-14-0883).

Author information

Authors and Affiliations

  1. Department of Organic Chemistry, Institute of Chemical Sciences, P. J. Šafárik University, Moyzesova 11, 040 01, Košice, Slovak Republic

    Miroslav Psotka, Miroslava Martinková & Jozef Gonda

Authors
  1. Miroslav Psotka
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Miroslava Martinková
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jozef Gonda
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jozef Gonda.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Psotka, M., Martinková, M. & Gonda, J. A Lemieux–Johnson oxidation of shikimic acid derivatives: facile entry to small library of protected (2S,3S,4R)-2,3,4,7-tetrahydroxy-6-oxoheptanals. Chem. Pap. 71, 709–719 (2017). https://doi.org/10.1007/s11696-016-0004-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11696-016-0004-8

Keywords

Search

Navigation