CC BY-ND-NC 4.0 · SynOpen 2018; 02(03): 0251-0255
DOI: 10.1055/s-0037-1610365
Copyright with the author

First Stereoselective Total Synthesis of Tumonoic Acid A and its Derivatives

G. Nagalatha
Siva Ganesh Narala
A. Venkat Narsaiah*
SGN and GNL are grateful to UGC-New Delhi and CSIR-New Delhi, respectively, for providing Fellowships, the Ministry of Science and Technology for providing financial support under DST-SERB-GAP-0563 and the Director CSIR-IICT for providing facilities. IICT Commun. No: IICT/pubs./2018/268.
Further Information

Publication History

Received: 05 July 2018

Accepted after revision: 21 August 2018

Publication Date:
14 September 2018 (online)


An efficient protecting-group-free synthesis of tumonoic acid A and its derivatives has been accomplished. The synthesis started from commercially available n-octanal and employs the magnesium chloride catalysed anti-aldol reaction under the Evans protocol as the key step. Ethyl tumonoate A is a new tumonoic acid derivative with anti-inflammatory activity and inhibitory activity towards calcium oscillations in neocortical neurons.

Supporting Information

  • References

    • 1a Burja AM, Banaigs B, Mansour AE, Burgess JG, Wright PC. Tetrahedron 2001; 57: 9347
    • 1b Clark BR, Engene N, Teasdale ME, Rowley DC, Matainaho T, Valeriote FA, Gerwick WH. J. Nat. Prod. 2008; 71: 1530
    • 2a Tan LT. Phytochemistry 2007; 68: 954
    • 2b Gerwick WH, Coates RC, Engene N, Gerwick LG, Grindberg R, Jones A, Sorrels C. Microbe 2008; 3: 277
  • 3 Harrigan GG, Luesch H, Yoshida WY, Moore RE, Nagle DG, Biggs J, Park PU, Paul V. J. Nat. Prod. 1999; 62: 464
  • 4 Engene N, Choi H, Esquenazi E, Byrum T, Villa FA, Cao Z, Murray TF, Dorrestein PC, Gerwick L, Gerwick WH. J. Nat. Prod. 2011; 74: 1737
  • 5 Shiina I, Takasuna Y, Suzuki R, Oshiumi H, Komiyama Y, Hitomi S, Fukui H. Org. Lett. 2006; 8: 5279
    • 6a Calter MA, Liao W, Struss JA. J. Org. Chem. 2001; 66: 7500
    • 6b Handa M, Scheidt KA, Bossart M, Zheng N, Roush WR. J. Org. Chem. 2008; 73: 1031
    • 7a Evans DA, Tedrow JS, Shaw JT, Downey CW. J. Am. Chem. Soc. 2002; 124: 392
    • 7b Evans DA, Tedrow JS, Shaw JT, Downey CW. Org. Lett. 2002; 7: 1127
    • 7c Crimmins MT, King BW, Tabet EA, Chaudhary K. J. Org. Chem. 2001; 66: 894
    • 7d May AE, Connell NT, Dahlmann HA, Hoye TR. Synlett 2010; 1984
    • 7e Botubol JM, Sanchez AJ. M, Collado IG, Galan RH. Eur. J. Org. Chem. 2013; 2420
    • 8a Paik S, Carmeli S, Cullingham J, Moore RE, Patterson GM. L, Tius MA. J. Am. Chem. Soc. 1994; 116: 8116
    • 8b Pearson AJ, Zhang P. J. Org. Chem. 1996; 61: 9603
  • 9 Wang G, Goyal N, Hopkinson B. Bioorg. Med. Chem. Lett. 2009; 19: 3798