Synlett 2014; 25(1): 1-7
DOI: 10.1055/s-0033-1340153
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© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of (+)-Fusarisetin A: A Biomimetic Approach

Jun Yin
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N Zhongshan Road, Shanghai 200062, P. R. of China   Fax: +86(21)62604784   Email: shgao@chem.ecnu.edu.cn
,
Shuanhu Gao*
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N Zhongshan Road, Shanghai 200062, P. R. of China   Fax: +86(21)62604784   Email: shgao@chem.ecnu.edu.cn
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Further Information

Publication History

Received: 26 August 2013

Accepted after revision: 17 September 2013

Publication Date:
05 November 2013 (online)

Abstract

This article outlines our recent efforts to synthesize (+)-fusarisetin A, a naturally occurring 3-acyltetramic acid, by a route based on a hypothetical biosynthesis. Our research suggests that the biosynthesis of (+)-fusarisetin A might involve the aerobic oxidation of equisetin, possibly mediated by metal oxidants or by photochemically produced reactive oxygen species.

 
  • References

  • 1 Newman DJ. J. Nat. Prod. 2012; 75: 311
  • 2 Nicolaou KC, Montagnon T. Molecules That Changed the World: A Brief History of the Art and Science of Synthesis and Its Impact on Society. Wiley; Weinheim: 2008
    • 3a Hendrickson JB. J. Am. Chem. Soc. 1975; 97: 5784
    • 3b Gaich T, Baran PS. J. Org. Chem. 2010; 75: 4657
    • 4a Trost BM, Salzmann TN. J. Am. Chem. Soc. 1973; 95: 6840
    • 4b Trost BM. Science 1983; 219: 245
    • 4c Shenvi RA, O’Malley DP, Baran PS. Acc. Chem. Res. 2009; 42: 530

      For atom-economic synthesis, see:
    • 5a Trost BM. Science 1991; 254: 1471
    • 5b Trost BM. Angew. Chem. Int. Ed. Engl. 1995; 34: 259

    • For step-economic synthesis, see:
    • 5c Wender PA, Croatt MP, Witulski B. Tetrahedron 2006; 62: 7505
    • 5d Wender PA, Verma VA, Paxton TJ, Pillow TH. Acc. Chem. Res. 2008; 41: 40
    • 5e Wender PA, Miller BL. Nature 2009; 460: 197

    • For redox-economic synthesis, see:
    • 5f Richter JM, Ishihara Y, Masuda T, Whitefield BW, Llamas T, Pohjakallio A, Baran PS. J. Am. Chem. Soc. 2008; 130: 17938
    • 5g Burns NZ, Baran PS, Hoffmann RW. Angew. Chem. Int. Ed. 2009; 48: 2854
  • 6 For a review on tetramic acid type natural products, see: Royles BJ. L. Chem. Rev. 1995; 95: 1981
  • 7 Jang J.-H, Asami Y, Jang J.-P, Kim S.-O, Moon DO, Shin K.-S, Hashizume D, Muroi M, Saito T, Oh H, Kim BY, Osada H, Ahn JS. J. Am. Chem. Soc. 2011; 133: 6865

    • For total syntheses of fusarisetin A, see:
    • 8a Deng J, Zhu B, Lu Z, Yu H, Li A. J. Am. Chem. Soc. 2012; 134: 920
    • 8b Xu J, Caro-Diaz EJ. E, Trzoss L, Theodorakis EA. J. Am. Chem. Soc. 2012; 134: 5072
    • 8c Xu J, Caro-Diaz EJ. E, Lacoske MH, Hung C.-I, Jamora C, Theodorakis EA. Chem. Sci. 2012; 3: 3378
    • 8d Huang J, Fang L, Long R, Shi L.-L, Shen H.-J, Li C.-C, Yang Z. Org. Lett. 2013; 15: 4018
    • 9a Yin J, Wang C, Kong LL, Cai SJ, Gao SH. Angew. Chem. Int. Ed. 2012; 51: 7786
    • 9b Yin J, Kong LL, Wang C, Shi YB, Cai SJ, Gao SH. Chem. Eur. J. 2013; 19: 13040

    • For a review on progress in the synthesis of fusarisetin A, see:
    • 9c Yin J, Kong LL, Gao SH. Youji Huaxue 2013; 33: 259

      For the isolation of equisetin, see:
    • 10a Burmeister HR, Bennett GA, Vesonder RF, Hesseltine CW. Antimicrob. Agents Chemother. 1974; 5: 634
    • 10b Phillips NJ, Goodwin JT, Fraiman A, Cole RJ, Lynn DG. J. Am. Chem. Soc. 1989; 111: 8223
  • 11 Marfori EC, Kajiyama S, Fukusaki E, Kobayashi A. Z. Naturforsch., C 2002; 57: 465
  • 12 Putri SP, Kinoshita H, Ihara F, Igarashi Y, Nihira T. J. Antibiot. 2010; 63: 195

    • For reviews on the Diels–Alder reaction in total synthesis, see:
    • 13a Craig D. Chem. Soc. Rev. 1987; 16: 187
    • 13b Nicolaou KC, Snyder SA, Montagnon T, Vassilikogiannakis G. Angew. Chem. Int. Ed. 2002; 41: 1668

    • For a review on intramolecular Diels–Alder reactions in total synthesis, see:
    • 13c Takao K, Munakata R, Tadano K. Chem. Rev. 2005; 105: 4779

      For total syntheses of equisetin, see:
    • 14a Turos E, Audia JE, Danishefsky SJ. J. Am. Chem. Soc. 1989; 111: 8231
    • 14b Burke LT, Dixon DJ, Ley SV, Rodríguez F. Org. Lett. 2000; 2: 3611
    • 14c Burke LT, Dixon DJ, Ley SV, Rodríguez F. Org. Biomol. Chem. 2005; 3: 274
    • 14d Kumiko YK, Shindo M, Shishido K. Tetrahedron Lett. 2001; 42: 2517
  • 15 Nishikawa Y, Kitajima M, Kogure N, Takayama H. Tetrahedron 2009; 65: 1608

    • For reviews on Mn(III)-promoted radical reactions, see:
    • 16a Snider BB. Chem. Rev. 1996; 96: 339
    • 16b Melikyan GG. Org. React. (N. Y.) 1997; 49: 427

    • For a review on the mechanisms of Mn(OAc)3-based radical reactions, see:
    • 16c Snider BB. Tetrahedron 2009; 65: 10738
  • 17 For a review on Mn(III)-based peroxidation, see: Nishino H. Top. Heterocycl. Chem. 2006; 6: 39
  • 18 Gust D, Moore TA. Science 1989; 244: 35
    • 19a Cano-Yelo H, Deronzier A. J. Chem. Soc., Perkin Trans. 2 1984; 1093
    • 19b MacMillan DW. C. Nature 2008; 455: 304
    • 20a Zen J.-M, Liou S.-L, Kumar AS, Hsia M.-S. Angew. Chem. Int. Ed. 2003; 42: 577
    • 20b Zhang M, Chen C.-C, Ma W.-H, Zhao J.-C. Angew. Chem. Int. Ed. 2008; 47: 9730
    • 20c Zou YQ. L, Lu Q, Fu L, Chang NJ, Rong J, Chen JR, Xiao WJ. Angew. Chem. Int. Ed. 2011; 50: 7171
    • 20d Xuan J, Cheng Y, An J, Lu LQ, Zhang XX, Xiao WJ. Chem. Commun. 2011; 47: 8337
    • 20e Zou YQ, Chen JR, Liu XP, Lu LQ, Davis RL, Jørgensen KA, Xiao WJ. Angew. Chem. Int. Ed. 2012; 51: 784
    • 20f Su Y, Zhang L, Jiao N. Org. Lett. 2011; 13: 2168
    • 21a Wipf P, Graham TH, Xiao J. Pure Appl. Chem. 2007; 79: 753
    • 21b Dickinson BC, Chang CJ. Nat. Chem. Biol. 2011; 7: 504

      For reviews on singlet oxygen chemistry, see:
    • 22a Kearns DR. Chem. Rev. 1971; 71: 395
    • 22b Frimer AA. Chem. Rev. 1979; 79: 359
    • 22c George MV, Bhat V. Chem. Rev. 1979; 79: 447
    • 22d DeRosa MC, Crutchley RJ. Coord. Chem. Rev. 2002; 233–234: 351