3 Conclusion and Outlook
The review presented herein summarizes and updates some recent publications
about the formation of eight- to ten-membered cyclic ethers. The synthesis of these
systems represents a significant challenge, because both entropic and enthalpic
barriers hamper cyclization strategies. Therefore, a variety of strategies and
approaches have been developed in the last years to overcome these difficulties
and have been successfully applied to the total synthesis of important natural
products. Due to the large number of natural products containing medium-sized
cyclic ether motifs, more methods are likely to be developed to access these
structures in the future.
Acknowledgment ES thanks MICINN for a grant (CTQ2009-10478).
References
1. Faulkner DJ (2002) Nat Prod Rep 19: 1–48 and following reviews in the same series
2. Mandolini L (1987) Adv Phys Org Chem 22:1–111
3. Irie T, Suzuki M, Masamune T (1965) Tetrahedron Lett: 1091–1099
4. Chattopadhyay SK, Karmakar S, Biswas T, Majumdar KC, Rahaman H, Roy B (2007)
Tetrahedron 63:3919–3952
5. Yet L (2000) Chem Rev 100:2963–3008
6. Raveto JL, Regueiro A, Marine JD (1992) Tetrahedron Lett 33:3389–3392
7. Roxburgh CJ (1993) Tetrahedron 49:10749
8. Snyder NL, Haines HM, Peczuh MW (2006) Tetrahedron 62:9301–9320
9. Elliott MC, Williams EJ (2001) J Chem Soc Perkin 1: 2303–2340
10. Elliott MC (2002) J Chem Soc Perkin 1: 2301–2323
11. Nakamura I, Yamamoto Y (2004) Chem Rev 104:2127–2198
12. Inoue M (2005) Chem Rev 105:4379–4405
13. Nakata T (2005) Chem Rev 105:4314–4347
14. Sasaki M (2006) Recent advances in total synthesis of marine polycyclic ethers. In: Kiyota H
(ed) Topics in heterocyclic chemistry, vol 5. Springer, Heidelberg, pp 149–178
15. Fujiwara K (2006) Total synthesis of medium-ring ethers from laurencia red algae. In: Kiyota
H (ed) Topics in heterocyclic chemistry, vol 5. Springer, Heidelberg, pp 97–148
16. Kleinke AS, Webb D, Jamison TF (2012) Tetrahedron 68:6999–7018
17. Hoberg JO (1998) Tetrahedron 54:12631–12670
18. Shiina I (2007) Chem Rev 107:239–273
19. Parenty A, Moreau X, Niel G, Campagne JM (2013) Chem Rev. doi:10.1021/cr300129n
20. Maier ME (2000) Angew Chem Int Ed 39:2073–2077
21. Grubbs RH (2010) Metathesis in natural product synthesis. Wiley-VCH, Weinheim
22. Schrock RR (2009) Chem Rev 109:3211–3226
23. Vougioukalakis GC, Grubbs RH (2010) Chem Rev 110:1746–1787
24. Samojiowicz C, Bieniek GK, Grela K (2009) Chem Rev 109:3708–3742
25. Monsaert S, Vial AL, Drozdzak R, Der Voort PV, Verpoort F (2009) Chem Soc Rev
38:3360–3372
26. Hoveyda AH, Zhugralin AR (2007) Nature 450:243–251
364
E. Soriano and J. Marco-Contelles
The review presented herein summarizes and updates some recent publications
about the formation of eight- to ten-membered cyclic ethers. The synthesis of these
systems represents a significant challenge, because both entropic and enthalpic
barriers hamper cyclization strategies. Therefore, a variety of strategies and
approaches have been developed in the last years to overcome these difficulties
and have been successfully applied to the total synthesis of important natural
products. Due to the large number of natural products containing medium-sized
cyclic ether motifs, more methods are likely to be developed to access these
structures in the future.
Acknowledgment ES thanks MICINN for a grant (CTQ2009-10478).
References
1. Faulkner DJ (2002) Nat Prod Rep 19: 1–48 and following reviews in the same series
2. Mandolini L (1987) Adv Phys Org Chem 22:1–111
3. Irie T, Suzuki M, Masamune T (1965) Tetrahedron Lett: 1091–1099
4. Chattopadhyay SK, Karmakar S, Biswas T, Majumdar KC, Rahaman H, Roy B (2007)
Tetrahedron 63:3919–3952
5. Yet L (2000) Chem Rev 100:2963–3008
6. Raveto JL, Regueiro A, Marine JD (1992) Tetrahedron Lett 33:3389–3392
7. Roxburgh CJ (1993) Tetrahedron 49:10749
8. Snyder NL, Haines HM, Peczuh MW (2006) Tetrahedron 62:9301–9320
9. Elliott MC, Williams EJ (2001) J Chem Soc Perkin 1: 2303–2340
10. Elliott MC (2002) J Chem Soc Perkin 1: 2301–2323
11. Nakamura I, Yamamoto Y (2004) Chem Rev 104:2127–2198
12. Inoue M (2005) Chem Rev 105:4379–4405
13. Nakata T (2005) Chem Rev 105:4314–4347
14. Sasaki M (2006) Recent advances in total synthesis of marine polycyclic ethers. In: Kiyota H
(ed) Topics in heterocyclic chemistry, vol 5. Springer, Heidelberg, pp 149–178
15. Fujiwara K (2006) Total synthesis of medium-ring ethers from laurencia red algae. In: Kiyota
H (ed) Topics in heterocyclic chemistry, vol 5. Springer, Heidelberg, pp 97–148
16. Kleinke AS, Webb D, Jamison TF (2012) Tetrahedron 68:6999–7018
17. Hoberg JO (1998) Tetrahedron 54:12631–12670
18. Shiina I (2007) Chem Rev 107:239–273
19. Parenty A, Moreau X, Niel G, Campagne JM (2013) Chem Rev. doi:10.1021/cr300129n
20. Maier ME (2000) Angew Chem Int Ed 39:2073–2077
21. Grubbs RH (2010) Metathesis in natural product synthesis. Wiley-VCH, Weinheim
22. Schrock RR (2009) Chem Rev 109:3211–3226
23. Vougioukalakis GC, Grubbs RH (2010) Chem Rev 110:1746–1787
24. Samojiowicz C, Bieniek GK, Grela K (2009) Chem Rev 109:3708–3742
25. Monsaert S, Vial AL, Drozdzak R, Der Voort PV, Verpoort F (2009) Chem Soc Rev
38:3360–3372
26. Hoveyda AH, Zhugralin AR (2007) Nature 450:243–251
364
E. Soriano and J. Marco-Contelles