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Pure and Applied Chemistry

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Volume 86, Issue 7 (Jul 2014)

Issues

Efficient asymmetric syntheses of alkaloids and medicinally relevant molecules based on heterocyclic chiral building blocks

Ai-E Wang
  • Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China
  • Other articles by this author:
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/ Pei-Qiang Huang
  • Corresponding author
  • Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China
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  • Other articles by this author:
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Published Online: 2014-04-04 | DOI: https://doi.org/10.1515/pac-2013-1210

Abstract

In this report, we present recent progress in synthetic methodologies based on three heterocyclic chiral building blocks developed from our laboratories. The potential of these chiral building block-based methods in the concise asymmetric synthesis of alkaloids and medicinally interesting molecules has been demonstrated by the total syntheses of 8-aza-prostaglandin E1, 11-hydroxylated analogues of the lead compounds CP-734432 and PF-04475270, (+)-castanospermine, (+)-1-epi-castanospermine, 7-deoxy-6-epi-castanospermine as well as 9-epi-sessilifoliamide J.

Keywords: alkaloids; asymmetric synthesis; chiral building blocks; ICHC-24; synthetic methodology; total synthesis

Article note: A collection of invited papers based on presentations at the 24th International Congress on Heterocyclic Chemistry (ICHC-24), Shanghai, China, 8–13 September 2013.

Dedicated to Prof. Dr. Li-Xin Dai on occasion of his 90th birthday.

References

  • [1]

    D. J. Newman. J. Med. Chem. 51, 2589–2599 (2008).Google Scholar

  • [2]

    I. Paterson, E. A. Anderson. Science 310, 451–452 (2005).PubMedGoogle Scholar

  • [3]

    J. Xu, Q. Gu, H. B. Liu, J. J. Zhou, X. Z. Bu, Z. S. Huang, G. Lu, D. Li, D. Q. Wei, L. Wang, L. Q. Gu. Scientia Sinica Chim. 43, 18–34 (2013).Google Scholar

  • [4]

    The concept of building block is associated with the seminal concept of synthon advanced by Corey, see: (a) E. J. Corey. Pure Appl. Chem. 14, 19–38 (1967); (b) E. J. Corey, X.-M. Cheng. The Logic of Chemical Synthesis, Wiley, N.Y. (1989); The concept of chiral building block is associated with the seminal concept of chiron, proposed by Hanessian, see: (c) S. Hanessian. Pure Appl. Chem. 65, 1189–1204 (1993); (d) S. Hanessian, J. Franco, B. Larouche. Pure Appl. Chem. 62, 1887–1910 (1990); (e) S. Hanessian. Total Synthesis of Natural Products: The Chiron Approach, Pergamon Press, Oxford, (1983); see also: (f) S. Warren. Designing Organic Syntheses: The Synthon Approach, Wiley, N.Y. (1977).Google Scholar

  • [5]

    For previous accounts, see: (a) P.-Q. Huang. “Recent Advances on the Asymmetric Synthesis of Bioactive 2-Pyrrolidinone-related Compounds Starting from Enantiomeric Malic Acid”, in New Methods for the Asymmetric Synthesis of Nitrogen Heterocycles. J. L. Vicario, D. Badia, L. Carrillo (Eds.), pp. 197–222, Research Signpost, Kerala (2005); (b) P.-Q. Huang. Synlett 1133–1149 (2006).Google Scholar

  • [6]

    F. Marks, G. Furstenberger. Prostaglandins, Leukotrienes and Other Eicosanoids. From Biogenesis to Clinical Application, Wiley-VCH, Weinheim (1999).Google Scholar

  • [7]

    (a) For reviews on the syntheses of prostaglandins and analogues, see: (a) P. W. Collins, S. W. Djuric. Chem. Rev. 93, 1533–1564 (1993); (b) S. Das, S. Chandrasekhar, J. S. Yadav, R. Gree. Chem. Rev. 107, 3286–3337 (2007).CrossrefGoogle Scholar

  • [8]

    R. Noyori, M. Suzuki. Angew. Chem., Int. Ed. Engl. 23, 847–876 (1984).Google Scholar

  • [9]

    N. A. McGrath, M. Brichacek, J. T. Njardarson. J. Chem. Educ. 87, 1348–1349 (2010). (http://cbc.arizona.edu/njardarson/group/top-pharmaceuticals-poster).

  • [10]

    S. Togo, H.-C. Chen, T. Takahashi, T. Kubota, K. Matsuo, D. Morioka, K. Watanabe, H. Yamamoto, Y. Nagashima, H. Shimada. J. Surg. Res. 146, 66–72 (2008).Google Scholar

  • [11]

    D. R. Haubrich, J. P. Cruet, W. D. Reid. Br. J. Pharm. 48, 80–87 (1973).Google Scholar

  • [12]

    X.-G. Wang, A.-E Wang, Y. Hao, Y.-P. Ruan, P.-Q. Huang. J. Org. Chem. 78, 9488–9493 (2013).Google Scholar

  • [13]

    J.-L. Zheng, H. Liu, Y.-F. Zhang, W. Zhao, J.-S. Tong, Y.-P. Ruan, P.-Q. Huang. Tetrahedron: Asymmetry 22, 257–263 (2011).Google Scholar

  • [14]

    D. S. Brown, P. Charreau, T. Hansson, S. V. Ley. Tetrahedron 47, 1311–1328 (1991).Google Scholar

  • [15]

    T. Katsuki, K. B. Sharpless. J. Am. Chem. Soc. 102, 5974–5976 (1980).Google Scholar

  • [16]

    J. S. Yadav, T. Shekharam, V. R. Gadgil. J. Chem. Soc., Chem. Commun. 843–844 (1990).Google Scholar

  • [17]

    For a review on the recent developments on the olefin cross-metathesis, see: (a) S. J. Connon, S. Blechert. Angew. Chem. Int. Ed. 42, 1900–1923 (2003); For the use of the cross olefin metathesis strategy in the synthesis of analogues of prostaglandins, see: (b) S. H. Jacobo, C.-T. Chang, G.-J. Lee, J. A. Lawson, W. S. Powell, D. Pratico, G. A. FitzGerald, J. Rokach. J. Org. Chem. 71, 1370–1379 (2006); (c) N. A. Sheddan, J. Mulzer. Org. Lett. 8, 3101–3104 (2006).CrossrefGoogle Scholar

  • [18]

    K.-Z. Hu, J. Ma, S. Qiu, X. Zheng, P.-Q. Huang. J. Org. Chem. 78, 1790–1801 (2013).Google Scholar

  • [19]

    (a) D. J. Hart, Y. M. Tsai. J. Am. Chem. Soc. 104, 1430–1432 (1982); (b) M.-J. Chen, Y. M. Tsai. Tetrahedron 67, 1564–1574 (2011), and references cited therein.CrossrefGoogle Scholar

  • [20]

    (a) K. Gopalaiah, H. B. Kagan. New J. Chem. 32, 607–637 (2008); (b) H. B. Kagan. Tetrahedron 59, 10351–10372 (2003).Google Scholar

  • [21]

    D. Mazéas, T. Skrydstrup, J.-M. Beau. Angew. Chem. Int. Ed. 34, 909–912 (1995).Google Scholar

  • [22]

    P.-Q. Huang, Q.-F. Chen, C.-L. Chen, H.-Q. Zhang. Tetrahedron: Asymmetry 10, 3827–3832 (1999).Google Scholar

  • [23]

    S. Nahm, S. M. Weinreb. Tetrahedron Lett. 22, 3815–3818 (1981).Google Scholar

  • [24]

    E. J. Corey, R. K. Bakshi, S. Shibata. J. Am. Chem. Soc. 109, 5551–5553 (1987).Google Scholar

  • [25]

    For selected reviews on azasugars, see: (a) P. Compain, O. R. Martin. Iminosugars: From Synthesis to Therapeutic Applications, Wiley-VCH, New York (2007); (b) N. Asano, R. J. Nash, R. J. Molyneux, G. W. J. Fleet, Tetrahedron: Asymmetry 11, 1645–1680 (2000).Google Scholar

  • [26]

    B. G. Winchester. Tetrahedron: Asymmetry 20, 645–651 (2009).Google Scholar

  • [27]

    (a) L. D. Hohenschutz, E. A. Bell, P. J. Jewess, D. P. Leworthy, R. J. Pryce, E. Arnold, J. Clardy. Phytochemistry 20, 811–814 (1981); (b) R. J. Nash, L. E. Fellows, J. V. Dring, C. H. Stirton, D. Carter, M. P. Hegarty, E. A. Bell., Phytochemistry 27, 1403–1406 (1988); (c) R. Saul, J. J. Ghidoni, R. J. Molyneux, A. D. Elbein. Proc. Natl. Acad. Sci. USA 82, 93–97 (1985).Google Scholar

  • [28]

    For two reviews, see: (a) T. D. Heightman, A. T. Vasella, Angew. Chem. Int. Ed. 38, 750–770 (1999); (b) B. Winchester. Biochem. Soc. Trans. 20, 699–705 (1992).CrossrefGoogle Scholar

  • [29]

    (a) D. Durantel, C. Alotte, F. Zoulim. Curr. Opin. Invest. Drugs 8, 125–129 (2007); (b) M. S. Butler. Nat. Prod. Rep. 25, 475–516 (2008).Google Scholar

  • [30]

    For related approaches and attempts, see: (a) T. Gallagher, M. Giles, R. S. Subramanian, M. S. Hadley. J. Chem. Soc., Chem. Commun. 166–168 (1992); (b) G. Casiraghi, F. Ulgheri, P. Spanu, G. Rassu, L. Pinna, G. G. Fava, M. B. Ferrari, G. Pelosi. J. Chem. Soc., Perkin Trans. 1 2991–2997 (1993); (c) S. H. J. Thompson, R. S. Subramanian, J. K. Roberts, M. S. Hadley. J. Chem. Soc., Chem. Commun. 933–934 (1994); (d) R. Hunter, S. C. M. Rees-Jones, H. Su. Tetrahedron Lett. 48, 2819–2822 (2007); (e) R. Hunter, S. C. M. Rees-Jones, H. Su. Beilstein J. Org. Chem. 3, 38–43 (2007).Google Scholar

  • [31]

    P. Beak, W. K. Lee. J. Org. Chem. 58, 1109–1117 (1993).Google Scholar

  • [32]

    P.-Q. Huang, X. Zheng, S.-L. Wang, J.-L. Ye, L.-R. Jin, Z. Chen. Tetrahedron: Asymmetry 10, 3309–3317 (1999).Google Scholar

  • [33]

    For a previous study, see: P.-Q. Huang, T.-J. Wu, Y.-P. Ruan. Org. Lett. 5, 4341–4344 (2003).CrossrefGoogle Scholar

  • [34]

    For a recent review, see: G. Casiraghi, F. Zanardi, G. Appendino, G. Rassu. Chem. Rev. 100, 1929–1972 (2000).CrossrefGoogle Scholar

  • [35]

    G. Liu, T.-J. Wu, Y.-P. Ruan, P.-Q. Huang. Chem. Eur. J. 16, 5755–5768 (2010).Google Scholar

  • [36]

    (a) M.J. Schneider. “Pyridine and piperidine alkaloids: An update”, in Alkaloids: Chemical and Biochemical Perspectives. S. W. Pelletier (Ed.), vol. 10, pp. 155–299, Elsevier Science, Oxford (1996); (b) J. P. Michael. Nat. Prod. Rep. 16, 675–696 (1999).Google Scholar

  • [37]

    For selected reviews, see: (a) M. Amat, M. Perez, J. Bosch. Synlett 143–160 (2011); (b) M. A. Wijdeven, J. Willemsen, F. P. J. T. Rutjes. Eur. J. Org. Chem. 2831–2844 (2010); (c) C. Escolano, M. Amat, J. Bosch. Chem. Eur. J.12, 8198–8207 (2006); (d) N. Toyooka, H. Nemoto. “Synthetic Studies on Biologically Active Alkaloids Starting from Lactam-Type Chiral Building Blocks”, in Studies in Natural Products Chemistry. Atta-ur-Rahman (Eds.), vol. 29, pp. 419–448, Elsevier, Amsterdam (2003); (e) S. Joseph, D. Comins, Curr. Opin. Drug Discov. Develop. 5, 870–880 (2002); (f) M. D. Groaning, Meyers, A. I. Tetrahedron 56, 9843–9873 (2000); (g) H. P. Husson, J. Royer, Chem. Soc. Rev. 28, 383–394 (1999); (h) M. A. Ciufolini, C. Y. W. Hermann, Q. Dong, T. Shimizu, S. Swaminathan, N. Xi. Synlett 105–114 (1998).Google Scholar

  • [38]

    For selected recent examples, see: (a) R.-F. Yang, P.-Q. Huang. Chem. Eur. J. 16, 10319–10322 (2010); (b) R. Fu, J.-L.Ye, X.-J. Dai, Y.-P. Ruan, P.-Q. Huang. J. Org. Chem. 75, 4230–4243 (2010).Google Scholar

  • [39]

    (a) I. R. Morgan, A. Yazici, S. G. Pyne, B. W. Skelton. J. Org. Chem. 73, 2943–2946 (2008); (b) I. R. Morgan, A. Yazici, S. G. Pyne. Tetrahedron 64, 1409–1419 (2008); (c) S. Chooprayoon, C. Kuhakarn, P. Tuchinda, V. Reutraku, M. Pohmakotr. Org. Biomol. Chem. 9, 531–537 (2010); (d) M. J. Chen, Y. M. Tsai. Tetrahedron 67, 1564–1574 (2011).Google Scholar

  • [40]

    S.-C. Tuo, J.-L. Ye, A.-E Wang, S.-Y. Huang, P.-Q. Huang. Org. Lett. 13, 5270–5273 (2011).Google Scholar

  • [41]

    Y. Hitotsuyanagi, E. Takeda, H. Fukaya, K. Takeya. Tetrahedron Lett. 49, 7376–7379 (2008).Google Scholar

  • [42]

    For reviews/accounts on vinylogous Mannich reactions, see: (a) S. F. Martin. Pure Appl. Chem. 69, 571–576 (1997); (b) G. Casiraghi, F. Zanardi, G. Appendino, G. Rassu. Chem. Rev. 100, 1929–1972 (2000); (c) S. K. Bur, S. F. Martin. Tetrahedron 57, 3221–3242 (2001); (d) S. F. Martin. Acc. Chem. Res. 35, 895–904 (2002); See, also: (e) M. Arend, B. Westermann, N. Risch. Angew. Chem. Int. Ed. 37, 1044–1107 (1998); (f) S. K. Bur, S. F. Martin. Org. Lett. 2, 3445–3447 (2000).Google Scholar

  • [43]

    (a) K. Otsubo, J. Inanaga, M. Yamaguchi. Tetrahedron Lett. 27, 5763–5764 (1986); (b) S. Fukuzawa, A. Nakanishi, T. Fujinami, S. Sakai. J. Chem. Soc., Chem. Commun. 624–625 (1986).Google Scholar

  • [44]

    T. Satoh, K. Nanba, S. Suzuki. Chem. Pharm. Bull. 19, 817–820 (1971).Google Scholar

  • [45]

    W. P. Griffith, S. V. Ley, G. P. Whitcombe, A. D. White. J. Chem. Soc., Chem. Commun. 1625–1627 (1987).Google Scholar

About the article

Corresponding author: Pei-Qiang Huang, Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China, e-mail:


Published Online: 2014-04-04

Published in Print: 2014-07-22


Citation Information: Pure and Applied Chemistry, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1515/pac-2013-1210.

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