Sequential sp2-sp2 coupling reactions in polyene macrolide synthesis. A novel approach to macrolactin A

Tetrahedron Letters

Volumn 37, Issue 20, 1996, Pages 3501-3504

  Boyce, Richard J ^a   Pattenden, Gerald ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

MACROLACTIN A; MACROLIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

LATEOLABRAX JAPONICUS;

EID: 0029974767     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00563-1     Document Type: Article

References (37)

1. Gustafson, K.; Roman, M; Fenical, W. J. Am. Chem. Soc., 1989, 111, 7519; Rychnovsky, S.D.; Skalitzky, D.J.; Pathirana, C.; Jensen, P.R.; Fenical, W. J. Am. Chem. Soc., 1992, 114, 671.
2. Gustafson, K.; Roman, M; Fenical, W. J. Am. Chem. Soc., 1989, 111, 7519; Rychnovsky, S.D.; Skalitzky, D.J.; Pathirana, C.; Jensen, P.R.; Fenical, W. J. Am. Chem. Soc., 1992, 114, 671.
3. Benvegnu, T.; Schio, L.; Le Floc'h, Y.; Grée, R. Synlett, 1994, 505; Donaldson, W.A.; Bell, P.T.; Wang, Z.; Bennett, D.W. Tetrahedron Lett., 1994, 35, 5829; Tanimori, S.; Morita, Y.; Tsubota, M.; Nakayama, M. Syn. Commun., 1996, 26, 559.
4. Benvegnu, T.; Schio, L.; Le Floc'h, Y.; Grée, R. Synlett, 1994, 505; Donaldson, W.A.; Bell, P.T.; Wang, Z.; Bennett, D.W. Tetrahedron Lett., 1994, 35, 5829; Tanimori, S.; Morita, Y.; Tsubota, M.; Nakayama, M. Syn. Commun., 1996, 26, 559.
5. Benvegnu, T.; Schio, L.; Le Floc'h, Y.; Grée, R. Synlett, 1994, 505; Donaldson, W.A.; Bell, P.T.; Wang, Z.; Bennett, D.W. Tetrahedron Lett., 1994, 35, 5829; Tanimori, S.; Morita, Y.; Tsubota, M.; Nakayama, M. Syn. Commun., 1996, 26, 559.
6. For reviews see: Stille, J.K Angew Chem. Int. Engl., 1986, 25, 508; Mitchell, T.N. Synthesis, 1992, 803; see also: Stille, J.K.; Tanaka, M. J. Am. Chem. Soc., 1987, 709, 3785; Stille, J.K.; Su, H.; Hill, D.H.; Schneider, P.; Tanaka, M.; Morrison, D.L.; Hegedus, L.S. Organometallics, 1991, 10, 1993; Gyorkos, A.C.; Stille, J.K.; Hegedus, L.S. J. Am. Chem. Soc., 1990, 112, 8465; Kalivretenos, A.; Stille, J.K.; Hegedus, L.S. J. Org. Chem., 1992, 56, 2883.
7. For reviews see: Stille, J.K Angew Chem. Int. Engl., 1986, 25, 508; Mitchell, T.N. Synthesis, 1992, 803; see also: Stille, J.K.; Tanaka, M. J. Am. Chem. Soc., 1987, 709, 3785; Stille, J.K.; Su, H.; Hill, D.H.; Schneider, P.; Tanaka, M.; Morrison, D.L.; Hegedus, L.S. Organometallics, 1991, 10, 1993; Gyorkos, A.C.; Stille, J.K.; Hegedus, L.S. J. Am. Chem. Soc., 1990, 112, 8465; Kalivretenos, A.; Stille, J.K.; Hegedus, L.S. J. Org. Chem., 1992, 56, 2883.
8. For reviews see: Stille, J.K Angew Chem. Int. Engl., 1986, 25, 508; Mitchell, T.N. Synthesis, 1992, 803; see also: Stille, J.K.; Tanaka, M. J. Am. Chem. Soc., 1987, 709, 3785; Stille, J.K.; Su, H.; Hill, D.H.; Schneider, P.; Tanaka, M.; Morrison, D.L.; Hegedus, L.S. Organometallics, 1991, 10, 1993; Gyorkos, A.C.; Stille, J.K.; Hegedus, L.S. J. Am. Chem. Soc., 1990, 112, 8465; Kalivretenos, A.; Stille, J.K.; Hegedus, L.S. J. Org. Chem., 1992, 56, 2883.
9. For reviews see: Stille, J.K Angew Chem. Int. Engl., 1986, 25, 508; Mitchell, T.N. Synthesis, 1992, 803; see also: Stille, J.K.; Tanaka, M. J. Am. Chem. Soc., 1987, 709, 3785; Stille, J.K.; Su, H.; Hill, D.H.; Schneider, P.; Tanaka, M.; Morrison, D.L.; Hegedus, L.S. Organometallics, 1991, 10, 1993; Gyorkos, A.C.; Stille, J.K.; Hegedus, L.S. J. Am. Chem. Soc., 1990, 112, 8465; Kalivretenos, A.; Stille, J.K.; Hegedus, L.S. J. Org. Chem., 1992, 56, 2883.
10. For reviews see: Stille, J.K Angew Chem. Int. Engl., 1986, 25, 508; Mitchell, T.N. Synthesis, 1992, 803; see also: Stille, J.K.; Tanaka, M. J. Am. Chem. Soc., 1987, 709, 3785; Stille, J.K.; Su, H.; Hill, D.H.; Schneider, P.; Tanaka, M.; Morrison, D.L.; Hegedus, L.S. Organometallics, 1991, 10, 1993; Gyorkos, A.C.; Stille, J.K.; Hegedus, L.S. J. Am. Chem. Soc., 1990, 112, 8465; Kalivretenos, A.; Stille, J.K.; Hegedus, L.S. J. Org. Chem., 1992, 56, 2883.
11. For reviews see: Stille, J.K Angew Chem. Int. Engl., 1986, 25, 508; Mitchell, T.N. Synthesis, 1992, 803; see also: Stille, J.K.; Tanaka, M. J. Am. Chem. Soc., 1987, 709, 3785; Stille, J.K.; Su, H.; Hill, D.H.; Schneider, P.; Tanaka, M.; Morrison, D.L.; Hegedus, L.S. Organometallics, 1991, 10, 1993; Gyorkos, A.C.; Stille, J.K.; Hegedus, L.S. J. Am. Chem. Soc., 1990, 112, 8465; Kalivretenos, A.; Stille, J.K.; Hegedus, L.S. J. Org. Chem., 1992, 56, 2883.
12. Pattenden, G.; Thom, S.M. Synlett, 1993, 215; see also Boden, C.; Pattenden, G. Synlett, 1994, 181.
13. Pattenden, G.; Thom, S.M. Synlett, 1993, 215; see also Boden, C.; Pattenden, G. Synlett, 1994, 181.
14. Some of the first examples of the intramolecular Stille reaction in synthesis were described by Piers et al, see: Piers, E.; Friesen, R.W.; Keay, B.A. J. Chem. Soc., Chem. Commun., 1985, 809; Piers, E.; Friesen, R.W. J. Org. Chem., 1986, 51, 3405; Piers, E.; Lu, Y.-F. J. Org. Chem., 1988, 53, 927.
15. Some of the first examples of the intramolecular Stille reaction in synthesis were described by Piers et al, see: Piers, E.; Friesen, R.W.; Keay, B.A. J. Chem. Soc., Chem. Commun., 1985, 809; Piers, E.; Friesen, R.W. J. Org. Chem., 1986, 51, 3405; Piers, E.; Lu, Y.-F. J. Org. Chem., 1988, 53, 927.
16. Some of the first examples of the intramolecular Stille reaction in synthesis were described by Piers et al, see: Piers, E.; Friesen, R.W.; Keay, B.A. J. Chem. Soc., Chem. Commun., 1985, 809; Piers, E.; Friesen, R.W. J. Org. Chem., 1986, 51, 3405; Piers, E.; Lu, Y.-F. J. Org. Chem., 1988, 53, 927.
17. See: Nicolaou, K.C.; Chakraborty, T.K.; Piscopio, A.D.; Minowa, N.; Bertinato, P. J. Am. Chem. Soc., 1993, 115, 4419; Barrett, A.G.M.; Boys, M.L.; Boehm, T.L. J. Org. Chem., 1996, 61, 685; McDermott, T.S.; Morlock, A.A.; Heathcock, C.H. J. Org. Chem., 1966, 61, 700; Adlington, R.M.; Baldwin, J.E.; Gansäuer, A.; McCoull, W.; Russell, A.T. J. Chem. Soc., Perkin Trans. 1., 1994, 1697; Hodgson, D.M.; Boulton, L.T.; Naw, G.N. Synlett, 1995, 267; Smith, A.B.; Condon, S.M.; McCaurley, J.A.; Leazer, J.L.; Leahy, J.W.; Maleczka, R.E. J. Am. Chem. Soc., 1995, 117, 5407.
18. See: Nicolaou, K.C.; Chakraborty, T.K.; Piscopio, A.D.; Minowa, N.; Bertinato, P. J. Am. Chem. Soc., 1993, 115, 4419; Barrett, A.G.M.; Boys, M.L.; Boehm, T.L. J. Org. Chem., 1996, 61, 685; McDermott, T.S.; Morlock, A.A.; Heathcock, C.H. J. Org. Chem., 1966, 61, 700; Adlington, R.M.; Baldwin, J.E.; Gansäuer, A.; McCoull, W.; Russell, A.T. J. Chem. Soc., Perkin Trans. 1., 1994, 1697; Hodgson, D.M.; Boulton, L.T.; Naw, G.N. Synlett, 1995, 267; Smith, A.B.; Condon, S.M.; McCaurley, J.A.; Leazer, J.L.; Leahy, J.W.; Maleczka, R.E. J. Am. Chem. Soc., 1995, 117, 5407.
19. See: Nicolaou, K.C.; Chakraborty, T.K.; Piscopio, A.D.; Minowa, N.; Bertinato, P. J. Am. Chem. Soc., 1993, 115, 4419; Barrett, A.G.M.; Boys, M.L.; Boehm, T.L. J. Org. Chem., 1996, 61, 685; McDermott, T.S.; Morlock, A.A.; Heathcock, C.H. J. Org. Chem., 1966, 61, 700; Adlington, R.M.; Baldwin, J.E.; Gansäuer, A.; McCoull, W.; Russell, A.T. J. Chem. Soc., Perkin Trans. 1., 1994, 1697; Hodgson, D.M.; Boulton, L.T.; Naw, G.N. Synlett, 1995, 267; Smith, A.B.; Condon, S.M.; McCaurley, J.A.; Leazer, J.L.; Leahy, J.W.; Maleczka, R.E. J. Am. Chem. Soc., 1995, 117, 5407.
20. See: Nicolaou, K.C.; Chakraborty, T.K.; Piscopio, A.D.; Minowa, N.; Bertinato, P. J. Am. Chem. Soc., 1993, 115, 4419; Barrett, A.G.M.; Boys, M.L.; Boehm, T.L. J. Org. Chem., 1996, 61, 685; McDermott, T.S.; Morlock, A.A.; Heathcock, C.H. J. Org. Chem., 1966, 61, 700; Adlington, R.M.; Baldwin, J.E.; Gansäuer, A.; McCoull, W.; Russell, A.T. J. Chem. Soc., Perkin Trans. 1., 1994, 1697; Hodgson, D.M.; Boulton, L.T.; Naw, G.N. Synlett, 1995, 267; Smith, A.B.; Condon, S.M.; McCaurley, J.A.; Leazer, J.L.; Leahy, J.W.; Maleczka, R.E. J. Am. Chem. Soc., 1995, 117, 5407.
21. See: Nicolaou, K.C.; Chakraborty, T.K.; Piscopio, A.D.; Minowa, N.; Bertinato, P. J. Am. Chem. Soc., 1993, 115, 4419; Barrett, A.G.M.; Boys, M.L.; Boehm, T.L. J. Org. Chem., 1996, 61, 685; McDermott, T.S.; Morlock, A.A.; Heathcock, C.H. J. Org. Chem., 1966, 61, 700; Adlington, R.M.; Baldwin, J.E.; Gansäuer, A.; McCoull, W.; Russell, A.T. J. Chem. Soc., Perkin Trans. 1., 1994, 1697; Hodgson, D.M.; Boulton, L.T.; Naw, G.N. Synlett, 1995, 267; Smith, A.B.; Condon, S.M.; McCaurley, J.A.; Leazer, J.L.; Leahy, J.W.; Maleczka, R.E. J. Am. Chem. Soc., 1995, 117, 5407.
22. See: Nicolaou, K.C.; Chakraborty, T.K.; Piscopio, A.D.; Minowa, N.; Bertinato, P. J. Am. Chem. Soc., 1993, 115, 4419; Barrett, A.G.M.; Boys, M.L.; Boehm, T.L. J. Org. Chem., 1996, 61, 685; McDermott, T.S.; Morlock, A.A.; Heathcock, C.H. J. Org. Chem., 1966, 61, 700; Adlington, R.M.; Baldwin, J.E.; Gansäuer, A.; McCoull, W.; Russell, A.T. J. Chem. Soc., Perkin Trans. 1., 1994, 1697; Hodgson, D.M.; Boulton, L.T.; Naw, G.N. Synlett, 1995, 267; Smith, A.B.; Condon, S.M.; McCaurley, J.A.; Leazer, J.L.; Leahy, J.W.; Maleczka, R.E. J. Am. Chem. Soc., 1995, 117, 5407.
23. Millar, J.G.; Oehlschlager, A.C. J. Org. Chem., 1984, 49, 2332.
24. All new compounds showed satisfactory spectroscopic data and mass spectrometric or microanalytical data.
25. Katsuki, T.; Lee, A.W.M.; Ma, P.; Martin, V.S.; Masamune, S.; Sharpless, K.B.; Tuddenham, D.; Walker, F.J. J. Org. Chem., 1982, 47, 1378.
26. Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc., 1986, 108, 7408.
27. Farina, V.; Krishnan, B. J. Am. Chem. Soc., 1991, 113, 9585.
28. Lane, C.F.; Myatt, H.L.; Daniels, J.; Hopps, H.B. J. Org. Chem., 1974, 39, 3052.
29. Stille, J.K.; Groh, B.L. J. Am. Chem. Soc., 1987, 109, 813.
30. Miyuaura, N.; Yamada, Y.; Suzuki, A. Tetrahedron Lett., 1979, 20, 3437; Miyuara, N.; Suiginome, H.; Suzuki, A. Tetrahedron Lett., 1981, 22, 127; Miyuara, N.; Suiginome, H.; Yamada, Y.; Suzuki, A. J. Am. Chem. Soc., 1985, 107, 972.
31. Miyuaura, N.; Yamada, Y.; Suzuki, A. Tetrahedron Lett., 1979, 20, 3437; Miyuara, N.; Suiginome, H.; Suzuki, A. Tetrahedron Lett., 1981, 22, 127; Miyuara, N.; Suiginome, H.; Yamada, Y.; Suzuki, A. J. Am. Chem. Soc., 1985, 107, 972.
32. Miyuaura, N.; Yamada, Y.; Suzuki, A. Tetrahedron Lett., 1979, 20, 3437; Miyuara, N.; Suiginome, H.; Suzuki, A. Tetrahedron Lett., 1981, 22, 127; Miyuara, N.; Suiginome, H.; Yamada, Y.; Suzuki, A. J. Am. Chem. Soc., 1985, 107, 972.
33. Uenishi, J.; Beau, J-M.; Armstrong, R.W.; Kishi, Y. J. Am. Chem. Soc., 1987, 109, 4756.
34. Hodgson, D.M.; Boulton, L.T.; Maw, G.N. Tetrahedron Lett., 1994, 35, 2231.
35. Alder, V-K.; Brochhagen, F.; Kaiser, C.; Roth, W. Liebigs Ann. Chem., 1955, 593, 1.
36. Guindon, Y.; Morton, H.E.; Yoakim, C. Tetrahedron Lett., 1983, 24, 3969.
37. These positional isomers were not fully separated and characterised.