Total Synthesis through Palladium-Catalyzed Bis-Cyclization of Bromoallenes

Part of the Springer Theses book series (Springer Theses)


Palladium(0)-catalyzed cyclization of bromoallenes bearing hydroxy and benzamide groups as internal nucleophiles stereoselectively provides functionalized tetrahydrofuran. This cyclization was expanded to divergent synthesis of pachastrissamine, a biologically active marine natural product, and its derivatives.


Flash Chromatography Grignard Reagent Alkyl Side Chain Intermolecular Reaction Bicyclic Compound 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


  1. 1.
    Kuroda I, Musman M, Ohtani I, Ichiba T, Tanaka J, Garcia-Gravalos D, Higa T (2002) J Nat Prod 65:1505–1506CrossRefGoogle Scholar
  2. 2.
    Ledroit V, Debitus C, Lavaud C, Massoit G (2003) Tetrahedron Lett 44:225–228CrossRefGoogle Scholar
  3. 3.
    Canals D, Mormeneo D, Fabriàs G, Llebaria A, Casas J, Delgado A (2009) Bioorg Med Chem 17:235–241CrossRefGoogle Scholar
  4. 4.
    Salma Y, Lafort E, Therville N, Carpentier S, Bonnafé M-J, Levade T, Génisson Y, Andrieu-Abadie N (2009) Biochem Pharmacol 78:477–485CrossRefGoogle Scholar
  5. 5.
    Sudhakar N, Kumar AR, Prabhakar A, Jagadeesh B, Rao BV (2005) Tetrahedron Lett 46:325–327CrossRefGoogle Scholar
  6. 6.
    Bhaket P, Morris K, Stauffer CS, Datta A (2005) Org Lett 7:875–876CrossRefGoogle Scholar
  7. 7.
    van den Berg R, Boltje T, Verhagen C, Litjens R, Vander Marel G, Overkleeft H (2006) J Org Chem 71:836–839CrossRefGoogle Scholar
  8. 8.
    Du Y, Liu J, Linhardt RJ (2006) J Org Chem 71:1251–1253CrossRefGoogle Scholar
  9. 9.
    Liu J, Du Y, Dong X, Meng S, Xiao J, Cheng L (2006) Carbohydr Res 341:2653–2657CrossRefGoogle Scholar
  10. 10.
    Ribes C, Falomir E, Carda M, Marco JA (2006) Tetrahedron 62:5421–5425CrossRefGoogle Scholar
  11. 11.
    Lee T, Lee S, Kwak YS, Kim D, Kim S (2007) Org Lett 9:429–432CrossRefGoogle Scholar
  12. 12.
    Reddy LVR, Reddy PV, Shaw AK (2007) Tetrahedron Asymmetr 18:542–546CrossRefGoogle Scholar
  13. 13.
    Ramana CV, Giri AG, Suryawanshi SB, Gonnade RG (2007) Tetrahedron Lett 48:265–268CrossRefGoogle Scholar
  14. 14.
    Prasad KR, Chandrakumar A (2007) J Org Chem 72:6312–6315CrossRefGoogle Scholar
  15. 15.
    Abraham E, Candela-Lena JI, Davies SG, Georgiou M, Nicholson RL, Roberts PM, Russell AJ, Snchez-Fernndez EM, Smith AD, Thomson JE (2007) Tetrahedron Asymmetr 18:2510–2513CrossRefGoogle Scholar
  16. 16.
    Yakura T, Sato S, Yoshimoto Y (2007) Chem Pharm Bull 55:1284–1286CrossRefGoogle Scholar
  17. 17.
    Abraham E, Brock EA, Candela-Lena JI, Davies SG, Georgiou M, Nicholson RL, Perkins JH, Roberts PM, Russell AJ, Snchez-Fernndez EM, Scott PM, Smith AD, Thomson JE (2008) Org Biomol Chem 6:1665–1673CrossRefGoogle Scholar
  18. 18.
    Passiniemi M, Koskinen AMP (2008) Tetrahedron Lett 49:980–983CrossRefGoogle Scholar
  19. 19.
    Venkatesan K, Srinivasan KV (2008) Tetrahedron Asymmetr 19:209–215CrossRefGoogle Scholar
  20. 20.
    Enders D, Terteryan V, Palecek J (2008) Synthesis 2278–2282Google Scholar
  21. 21.
    Ichikawa Y, Matsunaga K, Masuda T, Kotsuki H, Nakano K (2008) Tetrahedron 64:11313–11318CrossRefGoogle Scholar
  22. 22.
    Yoshimitsu Y, Inuki S, Oishi S, Fujii N, Ohno H (2010) J Org Chem 75:3843–3846CrossRefGoogle Scholar
  23. 23.
    Abraham E, Davies SG, Roberts PM, Russell AJ, Thomson JE (2008) Tetrahedron: Asymmetry 19:1027–1047CrossRefGoogle Scholar
  24. 24.
    Cook GR, Shanker PS (1998) Tetrahedron Lett 39:3405–3408CrossRefGoogle Scholar
  25. 25.
    Cook GR, Shanker PS (1998) Tetrahedron Lett 39:4991–4994CrossRefGoogle Scholar
  26. 26.
    Lee K-Y, Kim Y-H, Park M-S, Oh C-Y, Ham W-H (1999) J Org Chem 64:9450–9458CrossRefGoogle Scholar
  27. 27.
    Garner P (1984) Tetrahedron Lett 25:5855–5858CrossRefGoogle Scholar
  28. 28.
    Campbell AD, Raynham TM, Taylor RJK (1998) Synthesis 1707–1709Google Scholar
  29. 29.
    Herold P (1988) Helv Chim Acta 71:354–362CrossRefGoogle Scholar
  30. 30.
    Montury M, Goré J (1980) Synth Commun 10:873–879CrossRefGoogle Scholar
  31. 31.
    Elsevier CJ, Meijer J, Tadema G, Stehouwer PM, Bos HJT, Vermeer P (1982) J Org Chem 47:2194–2196CrossRefGoogle Scholar
  32. 32.
    D’Aniello F, Mann A, Taddei M, Wermuth C-G (1994) Tetrahedron Lett 35:7775–7778Google Scholar
  33. 33.
    D’Aniello F, Mann A, Schoenfelder A, Taddei M (1997) Tetrahedron 53:1447–1456CrossRefGoogle Scholar
  34. 34.
    Ohno H, Hamaguchi H, Ohata M, Tanaka T (2003) Angew Chem Int Ed 42:1749–1753CrossRefGoogle Scholar
  35. 35.
    Ohno H, Hamaguchi H, Ohata M, Kosaka S, Tanaka T (2004) J Am Chem Soc 126:8744–8754CrossRefGoogle Scholar
  36. 36.
    Ohno H, Okano A, Kosaka S, Tsukamoto K, Ohata M, Ishihara K, Maeda H, Tanaka T, Fujii N (2008) Org Lett 10:1171–1174CrossRefGoogle Scholar
  37. 37.
    Ghosh AK, Xi K (2007) Org Lett 9:4013–4016CrossRefGoogle Scholar
  38. 38.
    Evans PA, Cui J, Gharpure SJ, Polosukhin A, Zhang H-R (2003) J Am Chem Soc 125:14702–14703CrossRefGoogle Scholar
  39. 39.
    Kotsuki H, Kadota I, Ochi M (1990) J Org Chem 55:4417–4422CrossRefGoogle Scholar
  40. 40.
    Somfai P (1994) Tetrahedron 50:11315–11320CrossRefGoogle Scholar
  41. 41.
    Arnold LD, Drover JCG, Vedreras JC (1987) J Am Chem Soc 109:4649–4659CrossRefGoogle Scholar
  42. 42.
    Hümmer W, Dubois E, Gracza T, Jäger V (1997) Synthesis 634–642Google Scholar
  43. 43.
    Lipshutz BH, Crow R, Dimock SH, Ellsworth ELJ (1990) J Am Chem Soc 112:4063–4064CrossRefGoogle Scholar
  44. 44.
    Lipshutz BH, Ellsworth EL, Dimock SH, Smith RAKJ (1990) J Am Chem Soc 112:4404–4410CrossRefGoogle Scholar
  45. 45.
    Fronza G, Mele A, Pedrocchi-Fantoni G, Pizzi D, Servi S (1990) J Org Chem 55:6216–6219CrossRefGoogle Scholar

Copyright information

© Springer 2012

Authors and Affiliations

  1. 1.Graduate School of Pharmaceutical SciencesKyoto UniversityKyotoJapan

Personalised recommendations