γ-Regioselectivity of lithiated 2-buten-4-olide towards aromatic aldehydes: A simple synthesis of γ-arylidenebutenolides

Tetrahedron

Volumn 54, Issue 37, 1998, Pages 11297-11304

  Pohmakotr, Manat ^a   Tuchinda, Patoomratana ^a   Premkaisorn, Pornchai ^a   Reutrakul, Vichai ^a  

^a MAHIDOL UNIVERSITY   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BUTENOLIDE; HEMPA; LITHIUM;

ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE;

EID: 0032505193     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00669-3     Document Type: Article

References (26)

1. 1. Taken from the M. Sc. Thesis of PP, Mahidol University, 1998.
2. 2. Rao, Y.S. Chem. Rev. 1976, 76, 625-694.
3. 3. Knight, D.W. Contemp. Org. Synth. 1994, 1, 287-315.
4. 4. Negishi, E; Korata, M. Tetrahedron 1997, 53, 6707-6738.
5. 5. Casiraghi, G; Rassu, G. Synthesis 1995, 607-626.
6. 6. Jung, J.H.; Pummangura, S.; Chaichantipyuth, C.; Patarapanich, C.; Fanwick, P.E.; Chang, C.-J.; McLaughlin, J.L. Tetrahedron 1990,46, 5043-5053.
7. 7. Jung, J.H.; Pummangura, S.; Chaichantipyuth, C.; Patarapanich, C.; McLaughlin, J.L. Phytochemistry 1990, 29, 1667-1670.
8. 8. Jung, J.H.; Chang, C.-J.; Smith, D.L.; McLaughlin, J.L. J. Nat. Prod. 1991, 54, 500-505.
9. 9. Tuchinda, P.; Udchachon, J.; Reutrakul, V.; Santisuk, T.; Taylor, W.C.; Farnsworth, N.R.; Pezzuto, J.M.; Kinghorn, A.D. Phytochemistry 1991, 33, 2685-2689.
10. 10. Nasman, J.H. Org. Synth. Col. Vol. VII 1993, 396-402.
11. 11. Haynes, R.K.; Lam, W.W.-L.; Yeung, L.; Williams, I.D.; Ridley, R.C.; Starling, S.M; Vonwiller, S.C.; Hambley, T.W.; Lelandais, P. J. Org. Chem. 1997, 62, 4552-4553.
12. 2, a 52:48 mixture of the α-and γ-adducts could be isolated in 27% yield together with 12% yield of the bis-adduct.
13. 13. γ-Selectivity of the lithiated 3-isopropyl-2-buten-4-olide with steroidal aldehydes has been reported: McMorris, T.C.; Chavez, R.G.; Patil, P.A. J. Chem. Soc. Perkin Trans. 1 1996, 295-302; Donaubauer, J.R.; Greaves, A.M.; McMorris, T.C. J. Org. Chem. 1984, 49, 2833-2834.
14. 13. γ-Selectivity of the lithiated 3-isopropyl-2-buten-4-olide with steroidal aldehydes has been reported: McMorris, T.C.; Chavez, R.G.; Patil, P.A. J. Chem. Soc. Perkin Trans. 1 1996, 295-302; Donaubauer, J.R.; Greaves, A.M.; McMorris, T.C. J. Org. Chem. 1984, 49, 2833-2834.
15. 14. γ-Selectivity of the anions derived from tetronic acid derivatives: see for examples, Honda, T.; Kondoh, H.; Okuyama, A.; Hayakawa, T.; Tsubuki, M.; Nagase, H. Heterocycles 1992, 33, 67-72 and references cited therein; Honda, T.; Kondoh, H.; Okuyama, A.; Hayakawa, T.; Tsubuki, M. Chem. Lett. 1991, 1861-1864; Pelter, A.; Al-Bayati, R.; Ayoub, M.T.; Lewis, W.; Pardasani, P.; Hansei, R. J. Chem. Soc. Perkin Trans. 1 1987, 717-742; Kametani, T.; Katoh, T.; Tsubuki, M.; Honda, T. J. Am. Chem. Soc. 1986, 108, 7055-7060; Pelter, A.; Al-Bayati, R.; Lewis, W. Tetrahedron Lett. 1982, 23, 353-356.
16. 14. γ-Selectivity of the anions derived from tetronic acid derivatives: see for examples, Honda, T.; Kondoh, H.; Okuyama, A.; Hayakawa, T.; Tsubuki, M.; Nagase, H. Heterocycles 1992, 33, 67-72 and references cited therein; Honda, T.; Kondoh, H.; Okuyama, A.; Hayakawa, T.; Tsubuki, M. Chem. Lett. 1991, 1861-1864; Pelter, A.; Al-Bayati, R.; Ayoub, M.T.; Lewis, W.; Pardasani, P.; Hansei, R. J. Chem. Soc. Perkin Trans. 1 1987, 717-742; Kametani, T.; Katoh, T.; Tsubuki, M.; Honda, T. J. Am. Chem. Soc. 1986, 108, 7055-7060; Pelter, A.; Al-Bayati, R.; Lewis, W. Tetrahedron Lett. 1982, 23, 353-356.
17. 14. γ-Selectivity of the anions derived from tetronic acid derivatives: see for examples, Honda, T.; Kondoh, H.; Okuyama, A.; Hayakawa, T.; Tsubuki, M.; Nagase, H. Heterocycles 1992, 33, 67-72 and references cited therein; Honda, T.; Kondoh, H.; Okuyama, A.; Hayakawa, T.; Tsubuki, M. Chem. Lett. 1991, 1861-1864; Pelter, A.; Al-Bayati, R.; Ayoub, M.T.; Lewis, W.; Pardasani, P.; Hansei, R. J. Chem. Soc. Perkin Trans. 1 1987, 717-742; Kametani, T.; Katoh, T.; Tsubuki, M.; Honda, T. J. Am. Chem. Soc. 1986, 108, 7055-7060; Pelter, A.; Al-Bayati, R.; Lewis, W. Tetrahedron Lett. 1982, 23, 353-356.
18. 14. γ-Selectivity of the anions derived from tetronic acid derivatives: see for examples, Honda, T.; Kondoh, H.; Okuyama, A.; Hayakawa, T.; Tsubuki, M.; Nagase, H. Heterocycles 1992, 33, 67-72 and references cited therein; Honda, T.; Kondoh, H.; Okuyama, A.; Hayakawa, T.; Tsubuki, M. Chem. Lett. 1991, 1861-1864; Pelter, A.; Al-Bayati, R.; Ayoub, M.T.; Lewis, W.; Pardasani, P.; Hansei, R. J. Chem. Soc. Perkin Trans. 1 1987, 717-742; Kametani, T.; Katoh, T.; Tsubuki, M.; Honda, T. J. Am. Chem. Soc. 1986, 108, 7055-7060; Pelter, A.; Al-Bayati, R.; Lewis, W. Tetrahedron Lett. 1982, 23, 353-356.
19. 14. γ-Selectivity of the anions derived from tetronic acid derivatives: see for examples, Honda, T.; Kondoh, H.; Okuyama, A.; Hayakawa, T.; Tsubuki, M.; Nagase, H. Heterocycles 1992, 33, 67-72 and references cited therein; Honda, T.; Kondoh, H.; Okuyama, A.; Hayakawa, T.; Tsubuki, M. Chem. Lett. 1991, 1861-1864; Pelter, A.; Al-Bayati, R.; Ayoub, M.T.; Lewis, W.; Pardasani, P.; Hansei, R. J. Chem. Soc. Perkin Trans. 1 1987, 717-742; Kametani, T.; Katoh, T.; Tsubuki, M.; Honda, T. J. Am. Chem. Soc. 1986, 108, 7055-7060; Pelter, A.; Al-Bayati, R.; Lewis, W. Tetrahedron Lett. 1982, 23, 353-356.
20. 15. Plewe, M.; Schmidt, R.R. Synthesis, 1989, 534-536; Boukouvalas, J.; Maltais, F.; Lachance N. Tetrahedron Lett. 1994, 35, 7897-7900; Shing, T.K.M.; Tai, V.W.-F.; Tsui, H.-C. J. Chem. Soc. Chem. Commun., 1994, 1293-1294; Shing, T.K.M.; Tai, V.W.-F.; Tsui, H.-C.; Zhou, Z.-H. J. Org. Chem. 1995, 60, 3121-3130; Mukai, C.; Hirai, S.; Kim, I.J.; Kido, M.; Hanaoka, M. Tetrahedron 1996, 52, 6547-6560.
21. 15. Plewe, M.; Schmidt, R.R. Synthesis, 1989, 534-536; Boukouvalas, J.; Maltais, F.; Lachance N. Tetrahedron Lett. 1994, 35, 7897-7900; Shing, T.K.M.; Tai, V.W.-F.; Tsui, H.-C. J. Chem. Soc. Chem. Commun., 1994, 1293-1294; Shing, T.K.M.; Tai, V.W.-F.; Tsui, H.-C.; Zhou, Z.-H. J. Org. Chem. 1995, 60, 3121-3130; Mukai, C.; Hirai, S.; Kim, I.J.; Kido, M.; Hanaoka, M. Tetrahedron 1996, 52, 6547-6560.
22. 15. Plewe, M.; Schmidt, R.R. Synthesis, 1989, 534-536; Boukouvalas, J.; Maltais, F.; Lachance N. Tetrahedron Lett. 1994, 35, 7897-7900; Shing, T.K.M.; Tai, V.W.-F.; Tsui, H.-C. J. Chem. Soc. Chem. Commun., 1994, 1293-1294; Shing, T.K.M.; Tai, V.W.-F.; Tsui, H.-C.; Zhou, Z.-H. J. Org. Chem. 1995, 60, 3121-3130; Mukai, C.; Hirai, S.; Kim, I.J.; Kido, M.; Hanaoka, M. Tetrahedron 1996, 52, 6547-6560.
23. 15. Plewe, M.; Schmidt, R.R. Synthesis, 1989, 534-536; Boukouvalas, J.; Maltais, F.; Lachance N. Tetrahedron Lett. 1994, 35, 7897-7900; Shing, T.K.M.; Tai, V.W.-F.; Tsui, H.-C. J. Chem. Soc. Chem. Commun., 1994, 1293-1294; Shing, T.K.M.; Tai, V.W.-F.; Tsui, H.-C.; Zhou, Z.-H. J. Org. Chem. 1995, 60, 3121-3130; Mukai, C.; Hirai, S.; Kim, I.J.; Kido, M.; Hanaoka, M. Tetrahedron 1996, 52, 6547-6560.
24. 15. Plewe, M.; Schmidt, R.R. Synthesis, 1989, 534-536; Boukouvalas, J.; Maltais, F.; Lachance N. Tetrahedron Lett. 1994, 35, 7897-7900; Shing, T.K.M.; Tai, V.W.-F.; Tsui, H.-C. J. Chem. Soc. Chem. Commun., 1994, 1293-1294; Shing, T.K.M.; Tai, V.W.-F.; Tsui, H.-C.; Zhou, Z.-H. J. Org. Chem. 1995, 60, 3121-3130; Mukai, C.; Hirai, S.; Kim, I.J.; Kido, M.; Hanaoka, M. Tetrahedron 1996, 52, 6547-6560.
25. 16. Lu, X.; Haung, X.; Ma, S. Tetrahedron Lett. 1993, 34, 5963-5966; Kotora, M.; Negishi, E. Synthesis, 1997, 121-128.
26. 16. Lu, X.; Haung, X.; Ma, S. Tetrahedron Lett. 1993, 34, 5963-5966; Kotora, M.; Negishi, E. Synthesis, 1997, 121-128.