Synlett 2014; 25(14): 1953-1970
DOI: 10.1055/s-0033-1338641
account
© Georg Thieme Verlag Stuttgart · New York

Syntheses of Bioactive Natural Products and Natural-Product-Like Compounds Based on Their Key Structural Units

Hongbin Zhang*
Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, P. R. of China   Fax: +86(871)65035538   Email: zhanghb@ynu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 09 February 2014

Accepted after revision: 01 April 2014

Publication Date:
03 June 2014 (online)


Dedicated to Professor Lewis N. Mander on the occasion of his 75th birthday

Abstract

This account describes our recent efforts toward the syntheses of natural products and natural-product-like compounds. Developing new strategies based on the key structural unit present in a target molecule is our main focus in the journey leading to the total synthesis of natural products.

1 Introduction

2 Synthesis of Podophyllotoxin

3 Synthesis of Mesembrine

4 Synthesis of Hexahydropyrroloindole Alkaloids

5 Total Synthesis of Stenine

6 Synthesis of Brazilide A, Brazilin, and Aza-Brazilins

7 Synthesis of Important Structural Units Present in Natural Products and Pharmaceuticals

8 Summary

 
  • References

  • 1 Biomimetic Organic Synthesis . Vol. 1. Poupon E, Nay B. Wiley-VCH; Weinheim: 2011: 1-956
    • 2a Corey EJ. Angew. Chem. Int. Ed. 1991; 30: 455
    • 2b Corey EJ, Cheng XM. The Logic of Chemical Synthesis . John Wiley & Sons; New York: 1989: 1-96
    • 2c Corey EJ. Chem. Soc. Rev. 1988; 17: 111
  • 3 Wilson RM, Danishefsky SJ. J. Org. Chem. 2007; 72: 4293
  • 4 Sheldon RA, Arends I, Hanefeld U. Green Chemistry and Catalysis . Wiley-VCH; Weinheim: 2007: 1-433
    • 6a Saleem M, Kim HJ, Ali MS, Lee YS. Nat. Prod. Rep. 2005; 22: 696
    • 6b Silverberg LJ, Dillon JL, Vemishetti P, Sleezer PD, Discordia RP, Hartung KB, Gao Q. Org. Process Res. Dev. 2000; 4: 34
    • 6c Damayanthi Y, Lown JW. Curr. Med. Chem. 1998; 5: 205
    • 6d Hande KR. Eur. J. Cancer 1998; 34: 1514 ; and references therein

      For reviews, see:
    • 7a Sellars JD, Steel PG. Eur. J. Org. Chem. 2007; 3815
    • 7b Ward RS. Phytochem. Rev. 2004; 2: 391
    • 7c Ward RS. Synthesis 1992; 719
    • 7d Ward RS. Tetrahedron 1990; 46: 5029

    • For more recent syntheses of podophyllotoxin, see:
    • 7e Ting CP, Maimone TJ. Angew. Chem. Int. Ed. 2014; 53: 3115
    • 7f Takahashi M, Suzuki N, Ishikawa T. J. Org. Chem. 2013; 78: 3250
  • 8 Wu Y, Zhang H, Zhao Y, Zhao J, Chen J, Li L. Org. Lett. 2007; 9: 1199
    • 9a Alexakis A, Sedrani R, Mangeney P, Normant JF. Tetrahedron Lett. 1988; 29: 4411
    • 9b Frey LF, Tillyer RD, Caille A.-S, Tschaen DM, Dolling U.-H, Grabowski EJ. J, Reider PJ. J. Org. Chem. 1998; 63: 3120
    • 10a Agami C, Comesse S, Kadouri-Puchot C. J. Org. Chem. 2002; 67: 1496
    • 10b Collum DB. Acc. Chem. Res. 1992; 25: 448
  • 11 Wu Y, Zhao J, Chen J, Pan C, Li L, Zhang H. Org. Lett. 2009; 11: 597
    • 12a Popelak A, Lettenbauer G In The Alkaloids : Chemistry and Physiology . Vol. 9. Manske RH. F. Academic Press; New York: 1967: 467-482

    • For reviews on the synthesis of mesembrine see:
    • 12b Zhao Y, Zhou Y, Du F, Liang L, Zhang H. Chin. J. Org. Chem. 2010; 30: 47
    • 12c Stevens RV, Wentland MP. J. Am. Chem. Soc. 1968; 90: 5580
    • 12d For a very recent synthesis of mesembrine, see: Geoghegan K, Evans P. J. Org. Chem. 2013; 78: 3410
    • 14a Anthoni U, Christophersen C, Nielsen PH In Alkaloids: Chemical and Biological Perspectives . Vol. 13. Pelletier SW. Pergamon; London: 1999: 163-236
    • 14b Hino T, Nakagawa M In The Alkaloids: Chemistry and Pharmacology . Vol. 34. Brossi A. Academic Press; New York: 1989: 1-75
    • 14c For a recent review, see: Ruiz-Sanchis P, Savina SA, Albericio F, Álvarez M. Chem. Eur. J. 2011; 17: 1388

    • For selected recent syntheses of hexahydropyrrolo[2,3-b]indole alkaloids, see:
    • 14d Lin A, Yang J, Hashim M. Org. Lett. 2013; 15: 1950
    • 14e Zhang X, Yang Z.-P, Liu C, You S.-L. Chem. Sci. 2013; 4: 3239
    • 14f Miyamoto H, Hirano T, Okawa Y, Nakazaki A, Kobayashi S. Tetrahedron 2013; 69: 9481
    • 15a Matsuura T, Overman LE, Poon DJ. J. Am. Chem. Soc. 1998; 120: 6500
    • 15b Ashimori A, Matsuura T, Overman LE, Poon DJ. J. Org. Chem. 1993; 58: 6949
  • 16 Zhou Y, Zhao Y, Dai X, Liu J, Li L, Zhang H. Org. Biomol. Chem. 2011; 9: 4091
  • 17 Zhou Y, Xi Y, Zhao J, Sheng X, Zhang S, Zhang H. Org. Lett. 2012; 14: 3116
    • 18a A similar intermediate has been used for the synthesis of horsfiline, see: Trost BM, Brennan MK. Org. Lett. 2006; 8: 2027

    • For selected recent syntheses of esermethole, see:
    • 18b Araki K, Ozawa T, Yokoe H, Kanematsu M, Yoshida M, Shishido K. Org. Lett. 2013; 15: 200
    • 18c Zhan F, Liang G. Angew. Chem. Int. Ed. 2013; 52: 1266
    • 19a Pilli RA, Ferreira de Oliveira Md. C. Nat. Prod. Rep. 2000; 17: 117
    • 19b Pilli RA, Rosso GB, Ferreira de Oliveira Md. C In The Alkaloids: Chemistry and Biology . Vol. 62. Cordell GA. Academic Press; New York: 2005: 77-173
  • 20 For a very recent review, see: Chen J, Chen J, Xie Y, Liu N, Liu D, Zhang H. Chin. J. Org. Chem. 2013; 33: 1186
    • 21a Evans DA, Seidel D. J. Am. Chem. Soc. 2005; 127: 9958
    • 21b Evans DA, Mito S, Seidel D. J. Am. Chem. Soc. 2007; 129: 11583
  • 22 Chen J, Chen J, Xie Y, Zhang H. Angew. Chem. Int. Ed. 2012; 51: 1024
    • 23a Robinson R. Bull. Soc. Chim. Fr. 1958; 125
    • 23b Craig JC, Naik AR, Pratt R, Johnson E. J. Org. Chem. 1965; 30: 1573
    • 23c Yamahara CF. J, Shimokawa T, Kinjo J, Tomimatsu T, Nohara T. Phytochemistry 1985; 24: 2403
    • 23d Namikoshi M, Nakata H, Yamada H, Nagai M, Saitoh T. Chem. Pharm. Bull. 1987; 35: 2761
    • 23e Kim DS, Baek N, Oh SP, Jung KY, Lee IS, Lee H.-K. Phytochemistry 1997; 46: 177
    • 23f Yang BO, Ke C.-Q, He Z.-S, Yang Y.-P, Ye Y. Tetrahedron Lett. 2002; 43: 1731
    • 24a Huang Y, Zhang J, Pettus TR. R. Org. Lett. 2005; 7: 5841
    • 24b Yen C.-T, Nakagawa-Goto K, Hwang T.-L, Wu P.-C, Morris-Natschke S.-L, Lai W.-C, Bastow KF, Chang F.-R, Wu Y.-C, Lee K.-H. Bioorg. Med. Chem. Lett. 2010; 20: 1037
    • 24c Davis FA, Chen B.-C. J. Org. Chem. 1993; 58: 1751
  • 25 Wang X, Zhang H, Yang X, Zhao J, Pan C. Chem. Commun. 2013; 49: 5405
  • 26 Liang J, Chen J, Du F, Zeng X, Li L, Zhang H. Org. Lett. 2009; 11: 2820
  • 27 Xu Z, Huang K, Liu T, Xie M, Zhang H. Chem. Commun. 2011; 47: 4923
    • 28a Liang J, Chen J, Liu J, Li L, Zhang H. Chem. Commun. 2010; 46: 3666
    • 28b Pan Z, Liang J, Chen J, Yang X, Zhang H. Nat. Prod. Bioprospect. 2011; 1: 129
    • 29a Tsuda Y, Nakai A, Ito K, Suzuki F, Haruna M. Heterocycles 1984; 22: 1817

    • For very recent syntheses of demethoxyerythratidinone, see:
    • 29b Heller ST, Kiho T, Narayan AR. H, Sarpong R. Angew. Chem. Int. Ed. 2013; 52: 11129
    • 29c Kalaitzakis D, Montagnon T, Antonatou E, Vassilikogiannakis G. Org. Lett. 2013; 15: 3714