methods, radical-based processes, and multicomponent cascades. Interestingly,
new methods for the selective synthesis of non-anomeric spiroacetals have included
the use of chiral phosphoric acids and their derivatives in dehydrative cyclizations
as well as hydrogen bonding-driven kinetic spirocyclizations.
It is expected that as the structures of new spiroacetal-containing natural products come to light, so too will new developments in the methods for their synthesis.
References
1. Mead KT, Brewer BN (2003) Curr Org Chem 7(3):227–256
2. Aho JE, Pihko PM, Rissa TK (2005) Chem Rev 105(12):4406–4440
3. Raju BR, Saikia AK (2008) Molecules 13(8):1942–2038
4. Rizzacasa MA, Pollex A (2009) Org Biomol Chem 7(6):1053–1059
5. Sperry J, Wilson ZE, Rathwell DCK et al (2010) Nat Prod Rep 27(8):1117–1137
6. Carter RG, Kuiper DL (2011) Sci Synth Stereosel Synth 2:863–914
7. Wilsdorf M, Reissig HU (2012) Angew Chem Int Ed 51(38):9486–9488
8. McLeod MC, Brimble MA, Rathwell DCK et al (2012) Pure Appl Chem 84(6):1379–1390
9. Green JC, Burnett GLIV, Pettus TRR (2012) Pure Appl Chem 84(7):1621–1631
10. Deslongchamps P, Rowan DD, Pothier N et al (1981) Can J Chem 59(7):1105–1121
11. Deslongchamps P (1983) Stereoelectronic effects in organic chemistry. Pergamon Press,
New York
12. Kirby AJ (1983) The anomeric effect and related stereoelectronic effects at oxygen. SpringerVerlag Berlin, New York
13. Perron F, Albizati KF (1989) Chem Rev 89(7):1617–1661
14. Pothier N, Goldstein S, Deslongchamps P (1992) Helv Chim Acta 75(2):604–620
15. Palmes JA, Aponick A (2012) Synthesis. doi:10.1055/s-0032-1317489
16. Favre S, Vogel P, Gerber-Lemaire S (2008) Molecules 13(10):2570–2600
17. Capecchi T, de Koning CB, Michael JP (2000) J Chem Soc Perkin Trans 1(16):2681–2688
18. Ballini R, Petrini M, Rosini G (2008) Molecules 13(2):319–330
19. Doubsky J, Streinz L, Saman D et al (2004) Org Lett 6(26):4909–4911
20. Gaunt MJ, Jessiman AS, Orsini P et al (2003) Org Lett 5(25):4819–4822
21. Waters SP, Fennie MW, Kozlowski MC (2006) Tetrahedron Lett 47(30):5409–5413
22. Smith AB, Condon SM, McCauley JA (1998) Acc Chem Res 31(1):35–46
23. Enders D, Lenzen A (2003) Synlett (14):2185–2187
24. Smith AB, Adams CM (2004) Acc Chem Res 37(6):365–377
25. Smith AB, Wuest WM (2008) Chem Commun (45):5883–5895
26. Smith AB, Sfouggatakis C, Risatti CA et al (2009) Tetrahedron 65(33):6489–6509
27. Smith AB, Lin Q, Doughty VA et al (2009) Tetrahedron 65(33):6470–6488
28. Smith AB, Smits H, Kim DS (2010) Tetrahedron 66(33):6597–6605
29. Ollivier A, Sinibaldi ME, Toupet L et al (2010) Tetrahedron Lett 51(31):4147–4149
30. Goubert M, Canet I, Sinibaldi ME (2009) Tetrahedron 65(21):4182–4189
31. Yadav JS, Chetia L (2007) Org Lett 9(22):4587–4589
32. Tursun A, Canet I, Aboab B et al (2005) Tetrahedron Lett 46(13):2291–2294
33. Ardes-Guisot N, Ouled-Lahoucine B, Canet I et al (2007) Tetrahedron Lett 48
(48):8511–8513
34. Melendez J, Alonso F, Yus M (2006) Tetrahedron Lett 47(7):1187–1191
35. Ramu E, Rao BV (2008) Tetrahedron Asymmetry 19(15):1820–1823
36. De Greef M, Zard SZ (2007) Org Lett 9(9):1773–1776
37. Favre S, Gerber-Lemaire S, Vogel P (2007) Org Lett 9(24):5107–5110
Synthesis of 5,6- and 6,6-Spirocyclic Compounds
263
new methods for the selective synthesis of non-anomeric spiroacetals have included
the use of chiral phosphoric acids and their derivatives in dehydrative cyclizations
as well as hydrogen bonding-driven kinetic spirocyclizations.
It is expected that as the structures of new spiroacetal-containing natural products come to light, so too will new developments in the methods for their synthesis.
References
1. Mead KT, Brewer BN (2003) Curr Org Chem 7(3):227–256
2. Aho JE, Pihko PM, Rissa TK (2005) Chem Rev 105(12):4406–4440
3. Raju BR, Saikia AK (2008) Molecules 13(8):1942–2038
4. Rizzacasa MA, Pollex A (2009) Org Biomol Chem 7(6):1053–1059
5. Sperry J, Wilson ZE, Rathwell DCK et al (2010) Nat Prod Rep 27(8):1117–1137
6. Carter RG, Kuiper DL (2011) Sci Synth Stereosel Synth 2:863–914
7. Wilsdorf M, Reissig HU (2012) Angew Chem Int Ed 51(38):9486–9488
8. McLeod MC, Brimble MA, Rathwell DCK et al (2012) Pure Appl Chem 84(6):1379–1390
9. Green JC, Burnett GLIV, Pettus TRR (2012) Pure Appl Chem 84(7):1621–1631
10. Deslongchamps P, Rowan DD, Pothier N et al (1981) Can J Chem 59(7):1105–1121
11. Deslongchamps P (1983) Stereoelectronic effects in organic chemistry. Pergamon Press,
New York
12. Kirby AJ (1983) The anomeric effect and related stereoelectronic effects at oxygen. SpringerVerlag Berlin, New York
13. Perron F, Albizati KF (1989) Chem Rev 89(7):1617–1661
14. Pothier N, Goldstein S, Deslongchamps P (1992) Helv Chim Acta 75(2):604–620
15. Palmes JA, Aponick A (2012) Synthesis. doi:10.1055/s-0032-1317489
16. Favre S, Vogel P, Gerber-Lemaire S (2008) Molecules 13(10):2570–2600
17. Capecchi T, de Koning CB, Michael JP (2000) J Chem Soc Perkin Trans 1(16):2681–2688
18. Ballini R, Petrini M, Rosini G (2008) Molecules 13(2):319–330
19. Doubsky J, Streinz L, Saman D et al (2004) Org Lett 6(26):4909–4911
20. Gaunt MJ, Jessiman AS, Orsini P et al (2003) Org Lett 5(25):4819–4822
21. Waters SP, Fennie MW, Kozlowski MC (2006) Tetrahedron Lett 47(30):5409–5413
22. Smith AB, Condon SM, McCauley JA (1998) Acc Chem Res 31(1):35–46
23. Enders D, Lenzen A (2003) Synlett (14):2185–2187
24. Smith AB, Adams CM (2004) Acc Chem Res 37(6):365–377
25. Smith AB, Wuest WM (2008) Chem Commun (45):5883–5895
26. Smith AB, Sfouggatakis C, Risatti CA et al (2009) Tetrahedron 65(33):6489–6509
27. Smith AB, Lin Q, Doughty VA et al (2009) Tetrahedron 65(33):6470–6488
28. Smith AB, Smits H, Kim DS (2010) Tetrahedron 66(33):6597–6605
29. Ollivier A, Sinibaldi ME, Toupet L et al (2010) Tetrahedron Lett 51(31):4147–4149
30. Goubert M, Canet I, Sinibaldi ME (2009) Tetrahedron 65(21):4182–4189
31. Yadav JS, Chetia L (2007) Org Lett 9(22):4587–4589
32. Tursun A, Canet I, Aboab B et al (2005) Tetrahedron Lett 46(13):2291–2294
33. Ardes-Guisot N, Ouled-Lahoucine B, Canet I et al (2007) Tetrahedron Lett 48
(48):8511–8513
34. Melendez J, Alonso F, Yus M (2006) Tetrahedron Lett 47(7):1187–1191
35. Ramu E, Rao BV (2008) Tetrahedron Asymmetry 19(15):1820–1823
36. De Greef M, Zard SZ (2007) Org Lett 9(9):1773–1776
37. Favre S, Gerber-Lemaire S, Vogel P (2007) Org Lett 9(24):5107–5110
Synthesis of 5,6- and 6,6-Spirocyclic Compounds
263