10 Conclusions
Significant progress has been made in the development of new or the optimization
of old methods that target the synthesis of substituted tetrahydrofuran substrates. It
is expected that these efforts will continue with a focus on the application of the
methods described here along with the discovery of new methods that enable even
simpler starting materials to be used.
References
1. Pan J-Y, Chen S-L, Yang M-H, Wu J, Sinkkonen J, Zou K (2009) Nat Prod Rep 26:1251–1292
2. Ferrier RJ (1998) Carbohydr Chem 30:268–315
3. Liaw C-C, Wu T-Y, Chang F-R, Wu Y-C (2010) Planta Med 76:1390–1404
4. Lorente A, Lamariano-Merketegi J, Albericio F, Alvarez M (2013) Chem Rev. ASAP
5. For a review that covers the period up to 2005, see Wolfe JP, Hay MB (2006) Tetrahedron
63:261–290
6. Larsen CH, Ridgway BH, Shaw JT, Woerpel KA (1999) J Am Chem Soc 121:12208–12209
7. Kim H, Wooten CM, Park Y, Hong J (2007) Org Lett 9:3965–3968
8. Mitchell TA, Romo D (2007) J Org Chem 72:9053–9059
9. Mead KT, Pillai SK (1993) Tetrahedron Lett 34:6997
10. Yang HW, Romo D (1997) J Org Chem 62:4–5
11. Mitchell TA, Zhao C, Romo D (2008) J Org Chem 73:9544–9551
12. Gharpure SJ, Shukla MK, Vijayasree U (2009) Org Lett 11:5466–5469
13. Opalka S, Steinbacher J, Lambiris B, McQuade D (2011) J Org Chem 76:6503–6517
14. Donohoe TJ, Harris RM, Williams O, Hargaden GC, Burrows J, Parker J (2009) J Am Chem
Soc 131:12854–12861
15. Donohoe TJ, Williams O, Churchill GH (2008) Angew Chem Int Ed 47:2869–2871
16. Pohlhaus P, Johnson J (2005) J Org Chem 70:1057–1059
17. Smith AG, Slade MC, Johnson JS (2011) Org Lett 13:1996–1999
18. Pohlaus PD, Sanders SD, Parsons AT, Li W, Johnson JS (2008) J Am Chem Soc 130:
8642–8650
19. Yang G, Shen Y, Li K, Sun Y, Hua Y (2011) J Org Chem 76:229–233
20. Yang G, Sun Y, Shen Y, Chai Z, Zhou S, Chu J, Chai J (2013) J Org Chem 78. ASAP
21. Pohlhaus P, Johnson J (2005) J Am Chem Soc 127:16014–16015
22. Benfatti F, de Nanteuil F, Waser J (2012) Org Lett 14:386–389
23. Miyake T, Endo S, Moriyama T, Sakata K, Nishibayashi Y (2013) Angew Chem Int Ed 52:
1758–1762
24. Parsons AT, Johnson JS (2009) J Am Chem Soc 131:3122–3123
25. Campbell MJ, Johnson JS (2009) J Am Chem Soc 131:10370–10371
26. Sanders SD, Ruiz-Olalla A, Johnson JS (2009) Chem Commun: 5135–5137
27. Karadeolian A, Kerr MA (2010) J Org Chem 75:6830–6841
28. Shin C, Cavre SN, Pae AN, Cha JH, Koh HY, Chang MH, Choi JH, Cho YS (2005) Org Lett
7:3283–3285
29. Chavre SN, Choo H, Cha JH, Pae AN, Choi KI, Cho YS (2006) Org Lett 8:3617–3619
30. Masse CE, Panek JS (1995) Chem Rev 95:1293–1316
31. Micalizio GC, Roush WR (2000) Org Lett 2:461–464
32. Hodgson DM, Salik S (2012) Org Lett 14:4402–4405
33. Akiyama T, Funaki S, Fuchibe K (2006) Heterocycles 67:369–374
Synthesis of Substituted Tetrahydrofurans
39
Significant progress has been made in the development of new or the optimization
of old methods that target the synthesis of substituted tetrahydrofuran substrates. It
is expected that these efforts will continue with a focus on the application of the
methods described here along with the discovery of new methods that enable even
simpler starting materials to be used.
References
1. Pan J-Y, Chen S-L, Yang M-H, Wu J, Sinkkonen J, Zou K (2009) Nat Prod Rep 26:1251–1292
2. Ferrier RJ (1998) Carbohydr Chem 30:268–315
3. Liaw C-C, Wu T-Y, Chang F-R, Wu Y-C (2010) Planta Med 76:1390–1404
4. Lorente A, Lamariano-Merketegi J, Albericio F, Alvarez M (2013) Chem Rev. ASAP
5. For a review that covers the period up to 2005, see Wolfe JP, Hay MB (2006) Tetrahedron
63:261–290
6. Larsen CH, Ridgway BH, Shaw JT, Woerpel KA (1999) J Am Chem Soc 121:12208–12209
7. Kim H, Wooten CM, Park Y, Hong J (2007) Org Lett 9:3965–3968
8. Mitchell TA, Romo D (2007) J Org Chem 72:9053–9059
9. Mead KT, Pillai SK (1993) Tetrahedron Lett 34:6997
10. Yang HW, Romo D (1997) J Org Chem 62:4–5
11. Mitchell TA, Zhao C, Romo D (2008) J Org Chem 73:9544–9551
12. Gharpure SJ, Shukla MK, Vijayasree U (2009) Org Lett 11:5466–5469
13. Opalka S, Steinbacher J, Lambiris B, McQuade D (2011) J Org Chem 76:6503–6517
14. Donohoe TJ, Harris RM, Williams O, Hargaden GC, Burrows J, Parker J (2009) J Am Chem
Soc 131:12854–12861
15. Donohoe TJ, Williams O, Churchill GH (2008) Angew Chem Int Ed 47:2869–2871
16. Pohlhaus P, Johnson J (2005) J Org Chem 70:1057–1059
17. Smith AG, Slade MC, Johnson JS (2011) Org Lett 13:1996–1999
18. Pohlaus PD, Sanders SD, Parsons AT, Li W, Johnson JS (2008) J Am Chem Soc 130:
8642–8650
19. Yang G, Shen Y, Li K, Sun Y, Hua Y (2011) J Org Chem 76:229–233
20. Yang G, Sun Y, Shen Y, Chai Z, Zhou S, Chu J, Chai J (2013) J Org Chem 78. ASAP
21. Pohlhaus P, Johnson J (2005) J Am Chem Soc 127:16014–16015
22. Benfatti F, de Nanteuil F, Waser J (2012) Org Lett 14:386–389
23. Miyake T, Endo S, Moriyama T, Sakata K, Nishibayashi Y (2013) Angew Chem Int Ed 52:
1758–1762
24. Parsons AT, Johnson JS (2009) J Am Chem Soc 131:3122–3123
25. Campbell MJ, Johnson JS (2009) J Am Chem Soc 131:10370–10371
26. Sanders SD, Ruiz-Olalla A, Johnson JS (2009) Chem Commun: 5135–5137
27. Karadeolian A, Kerr MA (2010) J Org Chem 75:6830–6841
28. Shin C, Cavre SN, Pae AN, Cha JH, Koh HY, Chang MH, Choi JH, Cho YS (2005) Org Lett
7:3283–3285
29. Chavre SN, Choo H, Cha JH, Pae AN, Choi KI, Cho YS (2006) Org Lett 8:3617–3619
30. Masse CE, Panek JS (1995) Chem Rev 95:1293–1316
31. Micalizio GC, Roush WR (2000) Org Lett 2:461–464
32. Hodgson DM, Salik S (2012) Org Lett 14:4402–4405
33. Akiyama T, Funaki S, Fuchibe K (2006) Heterocycles 67:369–374
Synthesis of Substituted Tetrahydrofurans
39