CC BY-ND-NC 4.0 · Synthesis 2019; 51(01): 107-121
DOI: 10.1055/s-0037-1610377
short review
Copyright with the author

Syntheses of Cyclomarins – Interesting Marine Natural Products with Distinct Mode of Action towards Malaria and Tuberculosis

Alexander Kiefer
,
Further Information

Publication History

Received: 02 October 2018

Accepted: 12 October 2018

Publication Date:
07 November 2018 (eFirst)

Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

The cyclomarins are cyclic heptapeptides from marine streptomycetes containing four rather unusual amino acids. Interestingly, the cyclomarins address two completely different targets: ClpC1, a subunit of the caseinolytic protease of Mycobacterium tuberculosis (MTB), as well as PfAp3Aase of Plasmodium falciparum. Therefore, the cyclomarins are interesting lead structures for the development of drugs targeting tuberculosis and malaria. As a result, several synthetic protocols towards the synthesis of these unusual building blocks as well as the natural products themselves have been developed, which will be discussed in this review.

1 Introduction

2 Synthesis of the Building Blocks

3 Total Synthesis of Cyclomarin C by Yao and Co-workers

4 Total Synthesis of Cyclomarin A and C by Barbie and Kazmaier

5 Conclusion

 
  • References

  • 1 Newman DJ, Cragg GM. J. Nat. Prod. 2016; 79: 629
  • 2 Laraia L, Waldmann H. Drug Discovery Today Technol. 2017; 23: 75
  • 3 Rossiter SE, Fletcher MH, Wuest WM. Chem. Rev. 2017; 117: 12415
  • 4 Chellat MF, Raguž L, Riedl R. Angew. Chem. Int. Ed. 2016; 55: 6600 ; Angew. Chem. 2016, 128, 6710
  • 5 O’Connell KM. G, Hodgkinson JT, Sore HF, Welch M, Salmond GP. C, Spring DR. Angew. Chem. Int. Ed. 2013; 52: 10706 ; Angew. Chem. 2013, 125, 10904
  • 6 Wright GD. Nat. Prod. Rep. 2017; 34: 694
  • 7 Butler MS, Blaskovich MA, Cooper MA. J. Antibiot. (Tokyo) 2017; 70: 3
  • 8 Dang T, Süssmuth RD. Acc. Chem. Res. 2017; 50: 1566
  • 9 Renner MK, Shen Y.-C, Cheng X.-C, Jensen PR, Frankmoelle W, Kauffman CA, Fenical W, Lobkovsky E, Clardy J. J. Am. Chem. Soc. 1999; 121: 11273
  • 10 Pazoles CJ, Siegel SA. US 5759995, 1998
  • 11 Schmitt EK, Riwanto M, Sambandamurthy V, Roggo S, Miault C, Zwingelstein C, Krastel P, Noble C, Beer D, Rao SP. S, Au M, Niyomrattanakit P, Lim V, Zheng J, Jeffery D, Pethe K, Camacho LR. Angew. Chem. Int. Ed. 2011; 50: 5889
  • 12 Vasudevan D, Rao SP. S, Noble CG. J. Biol. Chem. 2013; 288: 30883
  • 13 Weinhäupl K, Brennich M, Kazmaier U, Lelievre J, Ballell L, Goldberg A, Schanda P, Fraga H. J. Biol. Chem. 2018; 293: 8379
  • 14 Bürstner N, Roggo S, Ostermann N, Blank J, Delmas C, Freuler F, Gerhartz B, Hinniger A, Hoepfner D, Liechty B, Mihalic M, Murphy J, Pistorius D, Rottmann M, Thomas JR, Schirle M, Schmitt EK. ChemBioChem 2015; 16: 2433
  • 15 Intaraudom C, Rachtawee P, Suvannakad R, Pittayakhajonwut P. Tetrahedron 2011; 67: 7593
  • 16 Schultz AW, Oh DC, Carney JR, Williamson RT, Udwary DW, Jensen PR, Gould SJ, Fenical W, Moore BS. J. Am. Chem. Soc. 2008; 130: 4507
  • 17 Qian Q, Schultz AW, Moore BS, Tanner ME. Biochemistry 2012; 51: 7733
  • 18 Schultz AW, Lewis CA, Luzung MR, Baran PS, Moore BS. J. Nat. Prod. 2010; 73: 373
  • 19 Haruhiko T, Takehiko T, Yoshihiro T, Fumiaki H. Chem. Lett. 1992; 21: 431
  • 20 Kikuchi M, Konno H. Org. Lett. 2014; 16: 4324
  • 21 Oku N, Gustafson KR, Cartner LK, Wilson JA, Shigematsu N, Hess S, Pannell LK, Boyd MR, McMahon JB. J. Nat. Prod. 2004; 67: 1407
  • 22 Ford PW, Gustafson KR, McKee TC, Shigematsu N, Maurizi LK, Pannell LK, Williams DE, Dilip de Silva E, Lassota P, Allen TM, Van Soest R, Andersen RJ, Boyd MR. J. Am. Chem. Soc. 1999; 121: 5899
  • 23 Plaza A, Gustchina E, Baker HL, Kelly M, Bewley CA. J. Nat. Prod. 2007; 70: 1753
  • 24 Ma J, Huang H, Xie Y, Liu Z, Zhao J, Zhang C, Jia Y, Zhang Y, Zhang H, Zhang T, Ju J. Nat. Commun. 2017; 8: 391
  • 25 Shibata M, Yamamoto H, Nakazawa K. Agric. Biol. Chem. 1962; 26: 228
  • 26 Higashide E, Shibata M, Yamamoto H, Nakazawa K, Iwasaki H, Ueyanagi J, Miyake A. Agric. Biol. Chem. 1962; 26: 234
  • 27 Ueda K, Xiao J, Doket N, Nakatsuka S. Biosci. Biotechnol. Biochem. 1992; 33: 5377
  • 28 Isogai A, Nakayama J, Takayama S, Kusai A, Suzuki A. Biosci. Biotechnol. Biochem. 1992; 56: 1079
  • 29 Sugiyama H, Shioiri T, Yokokawa F. Tetrahedron Lett. 2002; 43: 3489
  • 30 Wen SJ, Yao ZJ. Org. Lett. 2004; 6: 2721
  • 31 Wen SJ, Hu TS, Yao ZJ. Tetrahedron 2005; 61: 4931
  • 32 Barbie P, Kazmaier U. Org. Lett. 2016; 18: 204
  • 33 Barbie P, Kazmaier U. Org. Biomol. Chem. 2016; 14: 6036
  • 34 Barbie P, Kazmaier U. Org. Biomol. Chem. 2016; 14: 6055
  • 35 Schöllkopf U, Groth U, Deng C. Angew. Chem., Int. Ed., Engl. 1981; 20: 798
  • 36 Beulshausen T, Groth U, Schöllkopf U. Liebigs Ann. Chem. 1991; 1207
  • 37 Ireland RE, Liu L, Roper TD, Gleason JL. Tetrahedron 1997; 53: 13257
  • 38 Hajra S, Karmakar A. Tetrahedron Lett. 2004; 45: 3185
  • 39 Hajra S, Karmakar A, Bhowmick M. Tetrahedron: Asymmetry 2006; 17: 210
  • 40 Blaskovich MA, Lajoie GA. J. Am. Chem. Soc. 1993; 115: 5021
  • 41 Hansen DB, Joullié MM. Tetrahedron: Asymmetry 2005; 16: 3963
  • 42 Blanchette MA, Choy W, Davis JT, Essenfeld AP, Masamune S, Roush WR, Sakai T. Tetrahedron Lett. 1984; 25: 2183
  • 43 Harmon RE, Wellman G, Gupta SK. J. Org. Chem. 1973; 38: 11
  • 44 Evans DA, Britton TC, Ellman JA, Dorow RL. J. Am. Chem. Soc. 1990; 112: 4011
  • 45 Evans DA, Britton TC, Ellman JA. Tetrahedron Lett. 1987; 28: 6141
  • 46 Tarver JE, Terranova KM, Joullié MM. Tetrahedron 2004; 60: 10277
  • 47 Davis FA, Portonovo PS, Reddy RE, Chiu Y. J. Org. Chem. 1996; 61: 440
  • 48 Hansen DB, Starr ML, Tolstoy N, Joullié MM. Tetrahedron: Asymmetry 2005; 16: 3623
  • 49 Nevalainen M, Koskinen AM. P. Synlett 2001; 640
  • 50 Sathish K, Reddy GP. K, Mainkar PS, Chandrasekhar S. Tetrahedron: Asymmetry 2011; 22: 1568
  • 51 Zwick CR, Renata H. J. Am. Chem. Soc. 2018; 140: 1165
  • 52 Della Sala G, Izzo I, Spinella A. Synlett 2006; 1319
  • 53 Hansen DB, Lewis AS, Gavalas SJ, Joullié MM. Tetrahedron: Asymmetry 2006; 17: 15
  • 54 Barbie P, Kazmaier U. Org. Biomol. Chem. 2015; 13: 9267
  • 55 Piller FM, Metzger A, Schade MA, Haag BA, Gavryushin A, Knochel P. Chem. Eur. J. 2009; 15: 7192
  • 56 Luzung MR, Lewis CA, Baran PS. Angew. Chem. Int. Ed. 2009; 48: 7025
  • 57 Parikh JR, Doering W. vonE. J. Am. Chem. Soc. 1967; 89: 5505
  • 58 McDonald C, Holcomb H, Kennedy K, Kirkpatrick E, Leathers T, Vanemon P. J. Org. Chem. 1989; 54: 1213
  • 59 McGarvey GJ, Hiner RN, Matsubara Y, Oh T. Tetrahedron Lett. 1983; 24: 2733
  • 60 Corey EJ, Schmidt G. Tetrahedron Lett. 1979; 20: 399
  • 61 Crich D, Banerjee A. J. Org. Chem. 2006; 71: 7106
  • 62 Evans DA, Ripin DH. B, Halstead DP, Campos KR. J. Am. Chem. Soc. 1999; 121: 6816
    • 63a Kazmaier U, Krebs A. Angew. Chem., Int. Ed. Engl. 1995; 34: 2012 ; Angew. Chem. 1995, 107, 2213
    • 63b Krebs A, Kazmaier U. Tetrahedron Lett. 1996; 37: 7945
    • 63c Mues H, Kazmaier U. Synthesis 2001; 487
    • 63d Kazmaier U, Mues H, Krebs A. Chem. Eur. J. 2002; 8: 185
  • 64 Mooiweer HH, Hiemstra H, Speckamp WN. Tetrahedron 1991; 47: 3451
  • 65 Diago-Meseguer J, Palomo-Coll AL, Fernández-Lizarbe JR, Zugaza-Bilbao A. Synthesis 1980; 547
  • 66 Coste J, Le-Nguyen D, Castro B. Tetrahedron Lett. 1990; 31: 205
  • 67 Takahashi H, Tanahashi K, Higashiyma K, Onishi H. Chem. Pharm. Bull. 1986; 34: 479
  • 68 Schmidt U, Griesser H, Leitenberger V, Lieberknecht A, Mangold R, Meyer R, Riedl B. Synthesis 1992; 487
  • 69 Schmidt U, Leitenberger V, Griesser H, Schmidt J, Meyer R. Synthesis 1992; 1248
  • 70 Van den Berg M, Minnaard AJ, Schudde EP, Van Esch J, De Vries AH. M, De Vries JG, Feringa BL. J. Am. Chem. Soc. 2000; 122: 11539
  • 71 Panella L, Aleixandre AM, Kruidhof GJ, Robertus J, Feringa BL, De Vries JG, Minnaard AJ. J. Org. Chem. 2006; 71: 2026
  • 72 Johnson KF, Van Zeeland R, Stanley LM. Org. Lett. 2013; 15: 2798
  • 73 Powers JC. Tetrahedron Lett. 1965; 6: 655
  • 74 Knochel P, Singer RD. Chem. Rev. 1993; 93: 2117
  • 75 Kazlauskas RJ, Weissfloch AN. E, Rappaport AT, Cuccia LA. J. Org. Chem. 1991; 56: 2656
    • 76a Kazmaier U. Amino Acids 1996; 11: 283
    • 76b Kazmaier U. Liebigs Ann./Recl. 1997; 285
    • 76c Kazmaier U, Schneider C. Synthesis 1998; 1321
  • 77 Kazmaier U. Angew. Chem., Int. Ed. Engl. 1994; 33: 998
  • 78 Marti C, Carreira EM. J. Am. Chem. Soc. 2005; 127: 11505
  • 79 Peng L, Xu JC. J. Org. Chem. 2000; 65: 2951
  • 80 Li P. e-EROS Encycl. Reagents Org. Synth. 2003; 2
  • 81 Shendage DM, Fröhlich R, Haufe G. Org. Lett. 2004; 6: 3675
  • 82 Lemaire-Audoire S, Savignac M, Blart E, Pourcelot G, Genêt JP, Bernard JM. Tetrahedron Lett. 1994; 35: 8783