Regio- and stereoselective preparation of γ-alkylidenebutenolides or α-pyrones using a Stille reaction and palladium-catalysed oxacyclisation sequence

Tetrahedron Letters

Volumn 44, Issue 41, 2003, Pages 7633-7636

  Rousset, Séverine ^a   Abarbri, Mohamed ^a   Thibonnet, Jérôme ^a,b   Parrain, Jean Luc ^b   Duchêne, Alain ^a  

^a UNIVERSITÉ DE TOURS   (France)

^b AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Butenolides; Heteroannulation; Palladium catalyst; Pyran 2 one

Indexed keywords

2 PYRONE DERIVATIVE; ACETYLIDE; ALDEHYDE; BUTENOLIDE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL REACTION; CROSS REACTION; CYCLIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; STILLE REACTION;

EID: 0141741267     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.08.043     Document Type: Article

References (56)

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2. For reviews on butenolides, see: (a) Rao, Y. S. Chem. Rev. 1964, 64, 353; (b) Rao, Y. S. Chem. Rev. 1976, 76, 625; (c) Knight, D. W. Contemp. Org. Synth. 1994, 1, 287; (d) Negishi, E.; Kotora, M. Tetrahedron 1997, 53, 6707; (e) Brückner, R. Curr. Org. Chem. 2001, 5, 679; (f) Rossi, R.; Bellina, F. Targets Heterocyclic Syst. 2001, 5, 169; (g) Brückner, R. Chem. Commun. 2001, 141. For a discussion of the chemistry of α-pyrones, see: (h) Staunton, J. In Comprehensive Organic Chemistry; Sammes, P. G., Ed.; Pergamon Press: Oxford, England, 1979; Vol. 4, pp. 629-646. 2H-Pyran-2-one and its derivatives are commonly referred to as 2-pyrones or α-pyrones: (i) Posner, G. H. Acc. Chem. Res. 1987, 20, 72-78.
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16. For recent synthesis of butenolides using Pd or Ag catalysts, see: (a) Hanisch, I.; Brückner, R. Synlett 2000, 374; (b) Brückner, R.; Ohe, F. v d. New J. Chem. 2000, 659; (c) Siegel, K.; Brückner, R. Synlett 1999, 1227; (d) Xu, C.; Negishi, E. Tetrahedron Lett. 1999, 40, 431; (e) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387; (f) Görth, F. C.; Umland, A.; Brückner, R. Eur. J. Org. Chem. 1998, 1055; (g) Rossi, R.; Bellina, F.; Biagetti M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7799; (h) Rossi, R.; Bellina, F.; Biagetti, M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7599; (i) Rossi, R.; Bellina, F.; Mannina, L. Tetrahedron Lett. 1998, 39, 3017; (j) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135; (k) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367; (l) Kotora, M.; Negishi, E. Synthesis 1997, 201; (m) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1996, 61, 3238; (n) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1995, 60, 796; (o) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Heterocycles 1995, 41, 2587; (p) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Synlett 1995, 871.
17. For recent synthesis of butenolides using Pd or Ag catalysts, see: (a) Hanisch, I.; Brückner, R. Synlett 2000, 374; (b) Brückner, R.; Ohe, F. v d. New J. Chem. 2000, 659; (c) Siegel, K.; Brückner, R. Synlett 1999, 1227; (d) Xu, C.; Negishi, E. Tetrahedron Lett. 1999, 40, 431; (e) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387; (f) Görth, F. C.; Umland, A.; Brückner, R. Eur. J. Org. Chem. 1998, 1055; (g) Rossi, R.; Bellina, F.; Biagetti M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7799; (h) Rossi, R.; Bellina, F.; Biagetti, M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7599; (i) Rossi, R.; Bellina, F.; Mannina, L. Tetrahedron Lett. 1998, 39, 3017; (j) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135; (k) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367; (l) Kotora, M.; Negishi, E. Synthesis 1997, 201; (m) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1996, 61, 3238; (n) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1995, 60, 796; (o) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Heterocycles 1995, 41, 2587; (p) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Synlett 1995, 871.
18. For recent synthesis of butenolides using Pd or Ag catalysts, see: (a) Hanisch, I.; Brückner, R. Synlett 2000, 374; (b) Brückner, R.; Ohe, F. v d. New J. Chem. 2000, 659; (c) Siegel, K.; Brückner, R. Synlett 1999, 1227; (d) Xu, C.; Negishi, E. Tetrahedron Lett. 1999, 40, 431; (e) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387; (f) Görth, F. C.; Umland, A.; Brückner, R. Eur. J. Org. Chem. 1998, 1055; (g) Rossi, R.; Bellina, F.; Biagetti M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7799; (h) Rossi, R.; Bellina, F.; Biagetti, M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7599; (i) Rossi, R.; Bellina, F.; Mannina, L. Tetrahedron Lett. 1998, 39, 3017; (j) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135; (k) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367; (l) Kotora, M.; Negishi, E. Synthesis 1997, 201; (m) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1996, 61, 3238; (n) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1995, 60, 796; (o) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Heterocycles 1995, 41, 2587; (p) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Synlett 1995, 871.
19. For recent synthesis of butenolides using Pd or Ag catalysts, see: (a) Hanisch, I.; Brückner, R. Synlett 2000, 374; (b) Brückner, R.; Ohe, F. v d. New J. Chem. 2000, 659; (c) Siegel, K.; Brückner, R. Synlett 1999, 1227; (d) Xu, C.; Negishi, E. Tetrahedron Lett. 1999, 40, 431; (e) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387; (f) Görth, F. C.; Umland, A.; Brückner, R. Eur. J. Org. Chem. 1998, 1055; (g) Rossi, R.; Bellina, F.; Biagetti M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7799; (h) Rossi, R.; Bellina, F.; Biagetti, M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7599; (i) Rossi, R.; Bellina, F.; Mannina, L. Tetrahedron Lett. 1998, 39, 3017; (j) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135; (k) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367; (l) Kotora, M.; Negishi, E. Synthesis 1997, 201; (m) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1996, 61, 3238; (n) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1995, 60, 796; (o) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Heterocycles 1995, 41, 2587; (p) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Synlett 1995, 871.
20. For recent synthesis of butenolides using Pd or Ag catalysts, see: (a) Hanisch, I.; Brückner, R. Synlett 2000, 374; (b) Brückner, R.; Ohe, F. v d. New J. Chem. 2000, 659; (c) Siegel, K.; Brückner, R. Synlett 1999, 1227; (d) Xu, C.; Negishi, E. Tetrahedron Lett. 1999, 40, 431; (e) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387; (f) Görth, F. C.; Umland, A.; Brückner, R. Eur. J. Org. Chem. 1998, 1055; (g) Rossi, R.; Bellina, F.; Biagetti M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7799; (h) Rossi, R.; Bellina, F.; Biagetti, M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7599; (i) Rossi, R.; Bellina, F.; Mannina, L. Tetrahedron Lett. 1998, 39, 3017; (j) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135; (k) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367; (l) Kotora, M.; Negishi, E. Synthesis 1997, 201; (m) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1996, 61, 3238; (n) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1995, 60, 796; (o) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Heterocycles 1995, 41, 2587; (p) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Synlett 1995, 871.
21. For recent synthesis of butenolides using Pd or Ag catalysts, see: (a) Hanisch, I.; Brückner, R. Synlett 2000, 374; (b) Brückner, R.; Ohe, F. v d. New J. Chem. 2000, 659; (c) Siegel, K.; Brückner, R. Synlett 1999, 1227; (d) Xu, C.; Negishi, E. Tetrahedron Lett. 1999, 40, 431; (e) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387; (f) Görth, F. C.; Umland, A.; Brückner, R. Eur. J. Org. Chem. 1998, 1055; (g) Rossi, R.; Bellina, F.; Biagetti M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7799; (h) Rossi, R.; Bellina, F.; Biagetti, M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7599; (i) Rossi, R.; Bellina, F.; Mannina, L. Tetrahedron Lett. 1998, 39, 3017; (j) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135; (k) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367; (l) Kotora, M.; Negishi, E. Synthesis 1997, 201; (m) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1996, 61, 3238; (n) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1995, 60, 796; (o) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Heterocycles 1995, 41, 2587; (p) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Synlett 1995, 871.
22. For recent synthesis of butenolides using Pd or Ag catalysts, see: (a) Hanisch, I.; Brückner, R. Synlett 2000, 374; (b) Brückner, R.; Ohe, F. v d. New J. Chem. 2000, 659; (c) Siegel, K.; Brückner, R. Synlett 1999, 1227; (d) Xu, C.; Negishi, E. Tetrahedron Lett. 1999, 40, 431; (e) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387; (f) Görth, F. C.; Umland, A.; Brückner, R. Eur. J. Org. Chem. 1998, 1055; (g) Rossi, R.; Bellina, F.; Biagetti M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7799; (h) Rossi, R.; Bellina, F.; Biagetti, M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7599; (i) Rossi, R.; Bellina, F.; Mannina, L. Tetrahedron Lett. 1998, 39, 3017; (j) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135; (k) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367; (l) Kotora, M.; Negishi, E. Synthesis 1997, 201; (m) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1996, 61, 3238; (n) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1995, 60, 796; (o) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Heterocycles 1995, 41, 2587; (p) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Synlett 1995, 871.
23. For recent synthesis of butenolides using Pd or Ag catalysts, see: (a) Hanisch, I.; Brückner, R. Synlett 2000, 374; (b) Brückner, R.; Ohe, F. v d. New J. Chem. 2000, 659; (c) Siegel, K.; Brückner, R. Synlett 1999, 1227; (d) Xu, C.; Negishi, E. Tetrahedron Lett. 1999, 40, 431; (e) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387; (f) Görth, F. C.; Umland, A.; Brückner, R. Eur. J. Org. Chem. 1998, 1055; (g) Rossi, R.; Bellina, F.; Biagetti M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7799; (h) Rossi, R.; Bellina, F.; Biagetti, M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7599; (i) Rossi, R.; Bellina, F.; Mannina, L. Tetrahedron Lett. 1998, 39, 3017; (j) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135; (k) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367; (l) Kotora, M.; Negishi, E. Synthesis 1997, 201; (m) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1996, 61, 3238; (n) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1995, 60, 796; (o) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Heterocycles 1995, 41, 2587; (p) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Synlett 1995, 871.
24. For recent synthesis of butenolides using Pd or Ag catalysts, see: (a) Hanisch, I.; Brückner, R. Synlett 2000, 374; (b) Brückner, R.; Ohe, F. v d. New J. Chem. 2000, 659; (c) Siegel, K.; Brückner, R. Synlett 1999, 1227; (d) Xu, C.; Negishi, E. Tetrahedron Lett. 1999, 40, 431; (e) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387; (f) Görth, F. C.; Umland, A.; Brückner, R. Eur. J. Org. Chem. 1998, 1055; (g) Rossi, R.; Bellina, F.; Biagetti M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7799; (h) Rossi, R.; Bellina, F.; Biagetti, M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7599; (i) Rossi, R.; Bellina, F.; Mannina, L. Tetrahedron Lett. 1998, 39, 3017; (j) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135; (k) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367; (l) Kotora, M.; Negishi, E. Synthesis 1997, 201; (m) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1996, 61, 3238; (n) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1995, 60, 796; (o) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Heterocycles 1995, 41, 2587; (p) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Synlett 1995, 871.
25. For recent synthesis of butenolides using Pd or Ag catalysts, see: (a) Hanisch, I.; Brückner, R. Synlett 2000, 374; (b) Brückner, R.; Ohe, F. v d. New J. Chem. 2000, 659; (c) Siegel, K.; Brückner, R. Synlett 1999, 1227; (d) Xu, C.; Negishi, E. Tetrahedron Lett. 1999, 40, 431; (e) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387; (f) Görth, F. C.; Umland, A.; Brückner, R. Eur. J. Org. Chem. 1998, 1055; (g) Rossi, R.; Bellina, F.; Biagetti M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7799; (h) Rossi, R.; Bellina, F.; Biagetti, M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7599; (i) Rossi, R.; Bellina, F.; Mannina, L. Tetrahedron Lett. 1998, 39, 3017; (j) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135; (k) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367; (l) Kotora, M.; Negishi, E. Synthesis 1997, 201; (m) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1996, 61, 3238; (n) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1995, 60, 796; (o) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Heterocycles 1995, 41, 2587; (p) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Synlett 1995, 871.
26. For recent synthesis of butenolides using Pd or Ag catalysts, see: (a) Hanisch, I.; Brückner, R. Synlett 2000, 374; (b) Brückner, R.; Ohe, F. v d. New J. Chem. 2000, 659; (c) Siegel, K.; Brückner, R. Synlett 1999, 1227; (d) Xu, C.; Negishi, E. Tetrahedron Lett. 1999, 40, 431; (e) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387; (f) Görth, F. C.; Umland, A.; Brückner, R. Eur. J. Org. Chem. 1998, 1055; (g) Rossi, R.; Bellina, F.; Biagetti M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7799; (h) Rossi, R.; Bellina, F.; Biagetti, M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7599; (i) Rossi, R.; Bellina, F.; Mannina, L. Tetrahedron Lett. 1998, 39, 3017; (j) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135; (k) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367; (l) Kotora, M.; Negishi, E. Synthesis 1997, 201; (m) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1996, 61, 3238; (n) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1995, 60, 796; (o) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Heterocycles 1995, 41, 2587; (p) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Synlett 1995, 871.
27. For recent synthesis of butenolides using Pd or Ag catalysts, see: (a) Hanisch, I.; Brückner, R. Synlett 2000, 374; (b) Brückner, R.; Ohe, F. v d. New J. Chem. 2000, 659; (c) Siegel, K.; Brückner, R. Synlett 1999, 1227; (d) Xu, C.; Negishi, E. Tetrahedron Lett. 1999, 40, 431; (e) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387; (f) Görth, F. C.; Umland, A.; Brückner, R. Eur. J. Org. Chem. 1998, 1055; (g) Rossi, R.; Bellina, F.; Biagetti M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7799; (h) Rossi, R.; Bellina, F.; Biagetti, M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7599; (i) Rossi, R.; Bellina, F.; Mannina, L. Tetrahedron Lett. 1998, 39, 3017; (j) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135; (k) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367; (l) Kotora, M.; Negishi, E. Synthesis 1997, 201; (m) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1996, 61, 3238; (n) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1995, 60, 796; (o) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Heterocycles 1995, 41, 2587; (p) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Synlett 1995, 871.
28. For recent synthesis of butenolides using Pd or Ag catalysts, see: (a) Hanisch, I.; Brückner, R. Synlett 2000, 374; (b) Brückner, R.; Ohe, F. v d. New J. Chem. 2000, 659; (c) Siegel, K.; Brückner, R. Synlett 1999, 1227; (d) Xu, C.; Negishi, E. Tetrahedron Lett. 1999, 40, 431; (e) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387; (f) Görth, F. C.; Umland, A.; Brückner, R. Eur. J. Org. Chem. 1998, 1055; (g) Rossi, R.; Bellina, F.; Biagetti M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7799; (h) Rossi, R.; Bellina, F.; Biagetti, M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7599; (i) Rossi, R.; Bellina, F.; Mannina, L. Tetrahedron Lett. 1998, 39, 3017; (j) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135; (k) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367; (l) Kotora, M.; Negishi, E. Synthesis 1997, 201; (m) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1996, 61, 3238; (n) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1995, 60, 796; (o) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Heterocycles 1995, 41, 2587; (p) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Synlett 1995, 871.
29. For recent synthesis of butenolides using Pd or Ag catalysts, see: (a) Hanisch, I.; Brückner, R. Synlett 2000, 374; (b) Brückner, R.; Ohe, F. v d. New J. Chem. 2000, 659; (c) Siegel, K.; Brückner, R. Synlett 1999, 1227; (d) Xu, C.; Negishi, E. Tetrahedron Lett. 1999, 40, 431; (e) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387; (f) Görth, F. C.; Umland, A.; Brückner, R. Eur. J. Org. Chem. 1998, 1055; (g) Rossi, R.; Bellina, F.; Biagetti M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7799; (h) Rossi, R.; Bellina, F.; Biagetti, M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7599; (i) Rossi, R.; Bellina, F.; Mannina, L. Tetrahedron Lett. 1998, 39, 3017; (j) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135; (k) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367; (l) Kotora, M.; Negishi, E. Synthesis 1997, 201; (m) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1996, 61, 3238; (n) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1995, 60, 796; (o) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Heterocycles 1995, 41, 2587; (p) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Synlett 1995, 871.
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54. We unambiguously established the structure and stereochemistry of these new compounds by NMR techniques. See also Ref. 6 and Ref. 7.
55. 3, 50 MHz) δ (ppm): 14.5, 19.0, 23.0, 28.6, 29.6, 32.0, 41.5, 92.0, 121.0, 149.0, 155.7, 167.5. MS (70 eV): m/z=320 (M, 32), 193 (13), 175 (13), 124 (100), 55 (22), 43 (25), 41 (36), 39 (35).
56. For compounds 4 or 5, the structure and stereochemistry were also confirmed by NMR techniques and by some Stille cross-coupling reactions; it is well known that these reactions occur always with retention of configuration. A full paper describing all these new compounds will reported in due course.