Synthesis 2019; 51(11): 2252-2260
DOI: 10.1055/s-0037-1611796
short review
© Georg Thieme Verlag Stuttgart · New York

The Chemical Syntheses of Nannocystins

University at Albany, State University of New York, 1400 Washington Ave., Albany, NY 12222, USA   Email: zwang9@albany.edu
› Author Affiliations
Start-up funds from SUNY-Albany are greatly acknowledged.
Further Information

Publication History

Received: 12 March 2019

Accepted after revision: 21 March 2019

Publication Date:
17 April 2019 (eFirst)

Abstract

The broad and potent anticancer activity of the nannocystin family of natural products has attracted significant efforts toward their total syntheses. Currently, seven total syntheses of different members of the nannocystins have been reported. In this Short Review, different synthetic approaches are highlighted. The reported structure-activity relationship (SAR) studies will also be highlighted.

 
  • References

  • 1 Hoffmann H, Kogler H, Heyse W, Matter H, Caspers M, Schummer D, Klemke-Jahn C, Bauer A, Penarier G, Debussche L, Brönstrup M. Angew. Chem. Int. Ed. 2015; 54: 10145
  • 2 Krastel P, Roggo S, Schirle M, Ross NT, Perruccio F, Aspesi P, Aust T, Buntin K, Estoppey D, Liechty B, Mapa F, Memmert K, Miller H, Pan X, Riedl R, Thibaut C, Thomas J, Wagner T, Weber E, Xie X, Schmitt EK, Hoepfner D. Angew. Chem. Int. Ed. 2015; 54: 10149
  • 3 Sasikumar AN, Perez WB, Kinzy TG. Wiley Interdiscip. Rev. RNA 2012; 3: 543
  • 4 Berisio R, Ruggiero A, Vitagliano L. Isr. J. Chem. 2010; 50: 71
  • 5 Andersen GR, Nissen P, Nyborg J. Trends Biochem. Sci. 2003; 28: 434
  • 6 https://www.pharmamar.com/wp-content/uploads/2018/12/ PR_Approval-APLIDIN-Australia.pdf.
  • 7 Huang J, Wang Z. Org. Lett. 2016; 18: 4702
  • 8 Jain P, Antilla JC. J. Am. Chem. Soc. 2010; 132: 11884
    • 9a Devos A, Remion J, Frisque-Hesbain A.-M, Colens A, Ghosez L. J. Chem. Soc., Chem. Commun. 1979; 1180

    • For applications of the Ghosez reagent in total synthesis, see:
    • 9b Elbatrawi YM, Kang CW, Del Valle JR. Org. Lett. 2018; 20: 2707
    • 9c Li Q, Seiple IB. J. Am. Chem. Soc. 2017; 139: 13304
    • 9d Bailey AM, Wolfrum S, Carreira EM. Angew. Chem. Int. Ed. 2016; 55: 639
    • 9e Nakamura H, Tsukano C, Yasui M, Yokouchi S, Igarashi M, Takemoto Y. Angew. Chem. Int. Ed. 2015; 54: 3136
    • 9f Yu Z, Ely RJ, Morken JP. Angew. Chem. Int. Ed. 2014; 53: 9632
    • 9g Zhu W, Jimenez M, Jung W.-H, Camarco DP, Balachandran R, Vogt A, Day BW, Curran DP. J. Am. Chem. Soc. 2010; 132: 9175

      For reviews of RCM reactions in macrocyclization, see:
    • 10a Fürstner A. Chem. Commun. 2011; 6505
    • 10b Hoveyda AH, Zhugralin AR. Nature 2007; 450: 243
    • 10c Fürstner A. Science 2013; 341: 1229713
    • 10d Cheng-Sánchez I, Sarabia F. Synthesis 2018; 50: 3749
    • 10e Hoveyda AH, Malcolmson SJ, Meek SJ, Zhugralin AR. Angew. Chem. Int. Ed. 2010; 49: 34
  • 11 Liao L, Zhou J, Xu Z, Ye T. Angew. Chem. Int. Ed. 2016; 55: 13263
  • 12 Shirokawa S, Kamiyama M, Nakamura T, Okada M, Nakazaki A, Hosokawa S, Kobayashi S. J. Am. Chem. Soc. 2004; 126: 13604

    • For reviews, see:
    • 13a Willemse T, Schepens W, van Vlijmen HW. T, Maes BU. W, Ballet S. Catalysts 2017; 7: 74
    • 13b Nicolaou KC, Bulger PG, Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4442
    • 13c Taheri Kal Koshvandi A, Heravi MM, Momeni T. Appl. Organomet. Chem. 2018; 32: e4210
    • 13d Heravi MM, Hashemi E. Tetrahedron 2012; 68: 9145
  • 14 Yang Z, Xu X, Yang CH, Tian Y, Chen X, Lian L, Pan W, Su X, Zhang W, Chen Y. Org. Lett. 2016; 18: 5768
  • 15 Zhang Y.-H, Liu R, Liu B. Chem. Commun. 2017; 5549
  • 16 Liu Q, Hu P, He Y. J. Org. Chem. 2017; 82: 9217
  • 17 Gieseler MT, Kalesse M. Org. Lett. 2011; 13: 2430
  • 18 Poock C, Kalesse M. Org. Lett. 2017; 19: 4536
  • 19 El-Faham A, Albericio F. J. Pept. Sci. 2010; 16: 6
  • 20 Meng Z, Souillart L, Monks B, Huwyler N, Herrmann J, Müller R, Fürstner A. J. Org. Chem. 2018; 83: 6977
  • 21 Yang Y, Perry IB, Lu G, Liu P, Buchwald SL. Science 2016; 353: 144
  • 22 Heppekausen J, Stade R, Goddard R, Fürstner A. J. Am. Chem. Soc. 2010; 132: 11045
  • 23 Roşca D.-A, Radkowski K, Wolf LM, Wagh M, Goddard R, Thiel W, Fürstner A. J. Am. Chem. Soc. 2017; 139: 2443
  • 24 Huwyler N, Radkowski K, Rummelt SM, Fürstner A. Chem. Eur. J. 2017; 23: 12412
  • 25 Preindl J, Jouvin K, Laurich D, Seidel G, Fürstner A. Chem. Eur. J. 2016; 22: 237
  • 26 Sánchez-Murcia PA, Cortés-Cabrera Á, Gago F. J. Comput. Aided. Mol. Des. 2017; 31: 915
  • 27 Tian Y, Xu X, Ding Y, Hao X, Bai Y, Tang Y, Zhang X, Li Q, Yang Z, Zhang W, Chen Y. Eur. J. Med. Chem. 2018; 150: 626
  • 28 Tian Y, Ding Y, Xu X, Bai Y, Tang Y, Hao X, Zhang W, Chen Y. Tetrahedron Lett. 2018; 59: 3206