Total Synthesis through Palladium-Catalyzed Bis-Cyclization of Propargyl Chlorides and Carbonates

  • Shinsuke Inuki
Part of the Springer Theses book series (Springer Theses)


Palladium(0)-catalyzed cyclization of propargyl chlorides and carbonates bearing hydroxy and benzamide groups as internal nucleophiles stereoselectively provides functionalized tetrahydrofuran. Cyclization reactivity is dependent on the relative configuration of the benzamide and leaving groups, and on the nature of the leaving groups. This bis-cyclization was used as the key step in a short-step total synthesis of pachastrissamine.


Flash Chromatography Oily Residue Propargyl Alcohol Propargyl Bromide Rochelle Salt 
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.
    Herold P (1988) Helv Chim Acta 71:354–362CrossRefGoogle Scholar
  2. 2.
    De Jonghe S, Van Overmeire I, Van Calenbergh S, Hendrix C, Busson R, De Keukeleire D, Herdewijin P (2000) Eur J Org Chem 3177–3183Google Scholar
  3. 3.
    Roush DM, Patel MM (1985) Synth Commun 15:675–679Google Scholar
  4. 4.
    Freedman J, Vaal MJ, Huber EW (1991) J Org Chem 56:670–672CrossRefGoogle Scholar
  5. 5.
    Lipshutz BH, Miller TA (1990) Tetrahedron Lett 31:5253–5256CrossRefGoogle Scholar
  6. 6.
    Okuda M, Tomioka K (1994) Tetrahedron Lett 35:4585–4586CrossRefGoogle Scholar
  7. 7.
    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
  8. 8.
    Okano A, Tsukamoto K, Kosaka S, Maeda H, Oishi S, Tanaka T, Fujii N, Ohno H (2010) Chem Eur J 16:8410–8418CrossRefGoogle Scholar
  9. 9.
    Okano A, Oishi S, Tanaka T, Fujii N, Ohno H (2010) J Org Chem 75:3396–3400Google Scholar
  10. 10.
    Ohno H, Toda A, Takemoto Y, Fujii N, Ibuka T (1999) J Chem Soc Perkin Trans 1:2949–2962Google Scholar
  11. 11.
    Ohno H, Hamaguchi H, Ohata M, Tanaka T (2003) Angew Chem Int Ed 42:1749–1753CrossRefGoogle Scholar
  12. 12.
    Ohno H, Hamaguchi H, Ohata M, Kosaka S, Tanaka T (2004) J Am Chem Soc 126:8744–8754CrossRefGoogle Scholar
  13. 13.
    Hamaguchi H, Kosaka S, Ohno H, Tanaka T (2005) Angew Chem Int Ed 44:1513–1517CrossRefGoogle Scholar
  14. 14.
    Hamaguchi H, Kosaka S, Ohno H, Fujii N, Tanaka T (2007) Chem Eur J 13:1692–1708CrossRefGoogle Scholar
  15. 15.
    Ogoshi S, Tsutsumi K, Nishiguchi S, Kurosawa H (1995) J Organomet Chem 493:C19–C21CrossRefGoogle Scholar
  16. 16.
    Tsutsumi K, Ogoshi S, Nishiguchi S, Kurosawa H (1998) J Am Chem Soc 120:1938–1939CrossRefGoogle Scholar
  17. 17.
    Tsutsumi K, Kawase T, Kakiuchi K, Ogoshi S, Okada Y, Kurosawa H (1999) Bull Chem Soc Jpn 72:2687–2692CrossRefGoogle Scholar
  18. 18.
    Casey CP, Nash JR, Yi CS, Selmeczy AD, Chung S, Powell DR, Hayashi RK (1998) J Am Chem Soc 120:722–733CrossRefGoogle Scholar
  19. 19.
    Ogoshi S, Kurosawa H (2003) J Synth Org Chem Jpn 61:14–23CrossRefGoogle Scholar
  20. 20.
    Labrosse J-R, Lhoste P, Delbecq F, Sinou D (2003) Eur J Org Chem 2813–2822Google Scholar
  21. 21.
    Yoshida M, Fujita M, Ihara M (2003) Org Lett 5:3325–3327Google Scholar
  22. 22.
    Mikami K, Yoshida A (1997) Angew Chem Int Ed Engl 36:858–860CrossRefGoogle Scholar
  23. 23.
    Ogoshi S, Nishida T, Shinagawa T, Kurosawa H (2001) J Am Chem Soc 123:7164–7165CrossRefGoogle Scholar
  24. 24.
    Yoshida M, Gotou T, Ihara M (2004) Tetrahedron Lett 45:5573–5575CrossRefGoogle Scholar
  25. 25.
    Molander GA, Sommers EM, Baker SR (2006) J Org Chem 71:1563–1568CrossRefGoogle Scholar
  26. 26.
    Yoshida M, Hayashi M, Shishido K (2007) Org Lett 9:1643–1646CrossRefGoogle Scholar
  27. 27.
    Yoshida M, Okada T, Shishido K (2007) Tetrahedron 63:6996–7002CrossRefGoogle Scholar
  28. 28.
    Vaz B, Pereira R, Pérez M, Ávarez R, De Lera AR (2008) J Org Chem 73:6534–6541CrossRefGoogle Scholar
  29. 29.
    Crabtree RH, Felkin H, Morris GE (1977) J Organomet Chem 141:205–215CrossRefGoogle Scholar
  30. 30.
    Crabtree RH, Davis MW (1986) J Org Chem 51:2655–2661CrossRefGoogle Scholar
  31. 31.
    Lehr P, Billich A, Charpiot B, Ettmayer P, Scholz D, Rosenwirth B, Gstach H (1996) J Med Chem 39:2060–2067CrossRefGoogle Scholar
  32. 32.
    Nordin IC (1966) J Heterocycl Chem 3:531–532CrossRefGoogle Scholar
  33. 33.
    Wilson SR, Mao DT, Khatri HN (1980) Synth Commun 10:17–23CrossRefGoogle Scholar
  34. 34.
    Meyers AI, Himmelsbach RJ, Reuman M (1983) J Org Chem 48:4053–4058CrossRefGoogle Scholar
  35. 35.
    Nagamitsu T, Sunazuka T, Tanaka H, Omura S, Sprengeler PA, Smith AB III (1996) J Am Chem Soc 118:3584–3590CrossRefGoogle Scholar
  36. 36.
    Feldman KS, Cutarelli TD, Florio RD (2002) J Org Chem 67:8528–8537CrossRefGoogle Scholar

Copyright information

© Springer 2012

Authors and Affiliations

  1. 1.Graduate School of Pharmaceutical SciencesKyoto UniversityKyotoJapan

Personalised recommendations