functionalized THP scaffolds with high regio-, diastereo-, and enantioselectivity
(up to four contiguous chiral centers in a single step). The fabrication of THPs by
lactone/lactol functionalization remains an attractive method due to the ease of
access to lactols and lactones, mild reaction conditions, and the ability to construct
2,6-trans THPs. The scope of such ring-forming strategies has been established by
the total synthesis of a large number of structurally complex natural products.
Furthermore, emerging concepts and methods will continue to facilitate developments in this field.
References
1. Clarke PA, Santos S (2006) Eur J Org Chem: 2045–2053
2. Tietze LE, Kettschau G (1997) Top Curr Chem 189:1–120
3. Boivin TLB (1987) Tetrahedron 43:3309–3362
4. Carmely S, Kashman Y (1985) Tetrahedron Lett 26:511–514
5. Kobayashi M, Tanaka J, Katori T, Kitagawa I (1990) Chem Pharm Bull 38:2960–2966
6. D’Ambrosio M, Guerriero A, Debitus C, Pietra F (1996) Helv Chim Acta 79:51–60
7. Hegde VR, Puar MS, Dai P, Patel M, Gullo VP, Das PR, Bond RW, McPhail AT (2000)
Tetrahedron Lett 41:1351–1354
8. Pettit GR, Herald CL, Doubek DL, Herald DL, Arnold E, Clardy J (1982) J Am Chem Soc
104:6846–6848
9. Pettit GR, Kamano Y, Herald CL (1987) J Org Chem 52:2848–2854
10. Pettit GR, Chicacz ZA, Gao F, Herald CL, Boyd MR, Schmidt JM, Hooper JNA (1993) J Org
Chem 58:1302–1304
11. Pettit GR, Cichacz ZA, Gao F, Herald CL, Boyd MR (1993) J Chem Soc Chem Commun:
1166–1168
12. Searle PA, Molinski TF (1995) J Am Chem Soc 117:8126–8131
13. Fuwa H (2012) Heterocycles 85:1255
14. Banwell MG, Bissett BD, Bui CT, Pham HTT, Simpson GW (1998) Aust J Chem 51:9–18
15. Betancort JM, Martı ´n VS, Padro ´n JM, Palazo ´n JM, Ramı ´rez MA, Soler MA (1997) J Org
Chem 62:4570–4583
16. Ramı ´rez MA, Padro ´n JM, Palazo ´n JM, Martı ´n VS (1997) J Org Chem 62:4584–4590
17. Banwell, MG, Bui CT, Pham HTT, Simpson GW (1996) J Chem Soc Perkin 1: 967–969
18. Schneider C, Schuffenhauer A (2000) Eur J Org Chem 2000:73–82
19. Houk KN, Strozier RW (1973) J Am Chem Soc 95:4094–4096
20. Paterson I, Cumming JG, Ward RA, Lamboley S (1995) Tetrahedron 51:9393–9412
21. Paterson I, Smith JD, Ward RA (1995) Tetrahedron 51:9413–9436
22. Fettes A, Carreira EM (2002) Angew Chem Int Ed 41:4098–4101
23. Crimmins MT, Siliphaivanh P (2003) Org Lett 5:4641–4644
24. Laurent F, Reymond S, Capdevielle P, Cossy J (2007) Org Lett 9:2461–2464
25. Bhattacharjee A, Soltani O, De Brabander JK (2002) Org Lett 4:481–484
26. Park H, Kim H, Hong J (2011) Org Lett 13:3742–3745
27. Yadav JS, Bandyopadhyay A, Kunwar AC (2001) Tetrahedron Lett 42:4907–4911
28. Ball M, Bradshaw BJ, Dumeunier R, Gregson TJ, MacCormick S, Omori H, Thomas EJ
(2006) Tetrahedron Lett 47:2223–2227
29. Paterson I, Keown LE (1997) Tetrahedron Lett 38:5727–5730
30. Micalizio GC, Pinchuk AN, Roush WR (2000) J Org Chem 65:8730–8736
31. Lee CS, Forsyth CJ (1996) Tetrahedron Lett 37:6449–6452
32. Forsyth CJ, Ahmed F, Cink RD, Lee CS (1998) J Am Chem Soc 120:5597–5598
92
M.A. Perry et al.
(up to four contiguous chiral centers in a single step). The fabrication of THPs by
lactone/lactol functionalization remains an attractive method due to the ease of
access to lactols and lactones, mild reaction conditions, and the ability to construct
2,6-trans THPs. The scope of such ring-forming strategies has been established by
the total synthesis of a large number of structurally complex natural products.
Furthermore, emerging concepts and methods will continue to facilitate developments in this field.
References
1. Clarke PA, Santos S (2006) Eur J Org Chem: 2045–2053
2. Tietze LE, Kettschau G (1997) Top Curr Chem 189:1–120
3. Boivin TLB (1987) Tetrahedron 43:3309–3362
4. Carmely S, Kashman Y (1985) Tetrahedron Lett 26:511–514
5. Kobayashi M, Tanaka J, Katori T, Kitagawa I (1990) Chem Pharm Bull 38:2960–2966
6. D’Ambrosio M, Guerriero A, Debitus C, Pietra F (1996) Helv Chim Acta 79:51–60
7. Hegde VR, Puar MS, Dai P, Patel M, Gullo VP, Das PR, Bond RW, McPhail AT (2000)
Tetrahedron Lett 41:1351–1354
8. Pettit GR, Herald CL, Doubek DL, Herald DL, Arnold E, Clardy J (1982) J Am Chem Soc
104:6846–6848
9. Pettit GR, Kamano Y, Herald CL (1987) J Org Chem 52:2848–2854
10. Pettit GR, Chicacz ZA, Gao F, Herald CL, Boyd MR, Schmidt JM, Hooper JNA (1993) J Org
Chem 58:1302–1304
11. Pettit GR, Cichacz ZA, Gao F, Herald CL, Boyd MR (1993) J Chem Soc Chem Commun:
1166–1168
12. Searle PA, Molinski TF (1995) J Am Chem Soc 117:8126–8131
13. Fuwa H (2012) Heterocycles 85:1255
14. Banwell MG, Bissett BD, Bui CT, Pham HTT, Simpson GW (1998) Aust J Chem 51:9–18
15. Betancort JM, Martı ´n VS, Padro ´n JM, Palazo ´n JM, Ramı ´rez MA, Soler MA (1997) J Org
Chem 62:4570–4583
16. Ramı ´rez MA, Padro ´n JM, Palazo ´n JM, Martı ´n VS (1997) J Org Chem 62:4584–4590
17. Banwell, MG, Bui CT, Pham HTT, Simpson GW (1996) J Chem Soc Perkin 1: 967–969
18. Schneider C, Schuffenhauer A (2000) Eur J Org Chem 2000:73–82
19. Houk KN, Strozier RW (1973) J Am Chem Soc 95:4094–4096
20. Paterson I, Cumming JG, Ward RA, Lamboley S (1995) Tetrahedron 51:9393–9412
21. Paterson I, Smith JD, Ward RA (1995) Tetrahedron 51:9413–9436
22. Fettes A, Carreira EM (2002) Angew Chem Int Ed 41:4098–4101
23. Crimmins MT, Siliphaivanh P (2003) Org Lett 5:4641–4644
24. Laurent F, Reymond S, Capdevielle P, Cossy J (2007) Org Lett 9:2461–2464
25. Bhattacharjee A, Soltani O, De Brabander JK (2002) Org Lett 4:481–484
26. Park H, Kim H, Hong J (2011) Org Lett 13:3742–3745
27. Yadav JS, Bandyopadhyay A, Kunwar AC (2001) Tetrahedron Lett 42:4907–4911
28. Ball M, Bradshaw BJ, Dumeunier R, Gregson TJ, MacCormick S, Omori H, Thomas EJ
(2006) Tetrahedron Lett 47:2223–2227
29. Paterson I, Keown LE (1997) Tetrahedron Lett 38:5727–5730
30. Micalizio GC, Pinchuk AN, Roush WR (2000) J Org Chem 65:8730–8736
31. Lee CS, Forsyth CJ (1996) Tetrahedron Lett 37:6449–6452
32. Forsyth CJ, Ahmed F, Cink RD, Lee CS (1998) J Am Chem Soc 120:5597–5598
92
M.A. Perry et al.