Skip to main content
Log in

Stereoselective total synthesis of verbalactone

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

A simple and efficient route for the stereoselective total synthesis of verbalactone from commercially available inexpensive starting material d-mannitol using Barbier allylation, α-aminoxylation, and Yamaguchi macrolactonization as key steps is reported.

Graphical Abstract

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. Magiatis P, Spanakis D, Mitaku S, Tsitsa E, Mentis A, Harvala C (2001) J Nat Prod 64:1093

    Article  CAS  Google Scholar 

  2. Doshida J, Hasegawa H, Onuki H, Shimidzu N (1996) J Antibiot 49:1105

    Article  CAS  Google Scholar 

  3. Takano S, Seton M, Ogasawara K (1992) Tetrahedron Asymm 3:533

    Article  CAS  Google Scholar 

  4. Bennett F, Knight D, Fenton G (1991) J Chem Soc Perkin Trans 1:1543

    Article  Google Scholar 

  5. Bennett F, Knight D, Fenton G (1989) Heterocycles 29:639

    Article  CAS  Google Scholar 

  6. Yang YL, Falck JR (1982) Tetrahedron Lett 23:4305

    Article  CAS  Google Scholar 

  7. Gogoi S, Barua NC, Kalita B (2004) Tetrahedron Lett 45:5577

    Article  CAS  Google Scholar 

  8. Sharma GVM, Reddy ChG (2004) Tetrahedron Lett 45:7483

    Article  CAS  Google Scholar 

  9. Allais F, Louvel MC, Cossy J (2007) Synlett 18:451

    Google Scholar 

  10. Salunke GB, Shivakumar I, Gurjar MK (2009) Tetrahedron Lett 50:2048

    Article  CAS  Google Scholar 

  11. Garg A, Singh VK (2009) Tetrahedron 65:8677

    Article  CAS  Google Scholar 

  12. Das B, Laxmminarayana K, Krishnaiah M, Nandan Kumar D (2009) Helv Chim Acta 92:1840

    Article  CAS  Google Scholar 

  13. Sabitha G, Bhaskar V, Yadav JS (2008) Synth Commun 38:3129

    Article  CAS  Google Scholar 

  14. Wu JZ, Gao J, Ren GB, Zhen ZB, Zhang YH, Wu YK (2009) Tetrahedron 65:289

    Article  CAS  Google Scholar 

  15. Chatopadyay A, Mamdapur VR (1995) J Org Chem 60:585

    Article  Google Scholar 

  16. Hayashi Y, Yamaguchi J, Hibino K, Shoji M (2003) Tetrahedron Lett 44:8293

    Article  CAS  Google Scholar 

  17. List B (2002) Tetrahedron 58:5573

    Article  CAS  Google Scholar 

  18. Hayashi Y, Yamaguchi J, Sumiya T, Shoji M (2004) Angew Chem Int Ed 43:1112

    Article  CAS  Google Scholar 

  19. Inanaga J, Hirata K, Saeki H, Katsuki T, Yamaguchi M (1979) Bull Chem Soc Jpn 52:1989

    Article  CAS  Google Scholar 

  20. Vilanova C, Sánchez-Péris M, Roldán S, Dhotare B, Carda M, Chattopadhyay A (2013) Tetrahedron Lett 54:6562

    Article  CAS  Google Scholar 

  21. Chandrasekhar S, Sreelakshmi L (2012) Tetrahedron Lett 53:3233

    Article  CAS  Google Scholar 

  22. Bujaranipalli S, Eppa G, Das S (2013) Synlett 24:1117

    Article  CAS  Google Scholar 

  23. Kamal A, Reddy PV, Prabhakar S, Balakrishna M (2009) Tetrahedron Asymm 20:2861

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We are grateful to CSIR-IICT, Hyderabad for providing analytical facilities

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Rudraraju Ramesh Raju.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 2748 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Alluraiah, G., Sreenivasulu, R., Sreenivasa Murthy, I. et al. Stereoselective total synthesis of verbalactone. Monatsh Chem 145, 2019–2024 (2014). https://doi.org/10.1007/s00706-014-1272-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-014-1272-z

Keywords

Navigation