DBU-induced phenol-keto resonance in 3,5-dihydroxyphthalide: Regioselectivities in condensations with α,β-unsaturated aldehydes - Facile synthesis of bioactive natural and unnatural benzopyrans

Synlett

Volumn , Issue 7, 2004, Pages 1243-1246

  Mondal, Mukulesh ^a   Argade, Narshinha P ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

3,5 dihydroxyphthalide; Benzopyran synthesis; Phenol keto resonance; Regio selective condensation; , unsaturated aldehydes

Indexed keywords

ALDEHYDE DERIVATIVE; BENZOPYRAN DERIVATIVE; PHENOL DERIVATIVE; PHTHALIC ACID DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SYNTHESIS; METHYLATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY;

EID: 2942724622     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-825596     Document Type: Article

References (29)

1. NCL Communication No. 6659.
2. (a) Cui, C.-B.; Ubukata, M.; Kekaya, H.; Onose, R.; Okada, G.; Takahasi, I.; Isono, K.; Osada, H. J. Antibiotics 1996, 49, 216.
3. (b) Fukami, A.; Nakamura, T.; Kim, Y.-P.; Shiomi, K.; Hayashi, M.; Nagai, T.; Yomada, H.; Komiyama, K. J. Antibiotics 2000, 53, 1215.
4. (c) Kinoshita, K.; Sasaki, T.; Awata, M.; Takada, M.; Yaginuma, S. J. Antibiotics 1997, 50, 961.
5. (d) Dekker, K. A.; Inagaki, T.; Gootz, T. D.; Kaneda, K.; Nomura, E.; Sakakibara, T.; Sakemi, S.; Sugie, Y.; Yamauchi, Y.; Yoshikawa, N.; Kojima, N. J. Antibiotics 1997, 50, 833.
6. (e) Fürstner, A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990.
7. (f) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem. Int. Ed. 1998, 37, 2534; and references cited therein (2a-f).
8. (a) Nicolaou, K. C.; Evans, R. M.; Roecker, A. J.; Hughes, R.; Downes, M.; Pfefferkorn, J. A. Org. Biomol. Chem. 2003, 1, 908.
9. (b) Nicolaou, K. C.; Pfefferkorn, J. A.; Cao, G.-Q. Angew. Chem. Int. Ed. 2000, 39, 734.
10. (c) Nicolaou, K. C.; Cao, G.-Q.; Pfefferkorn, J. A. Angew. Chem. Int. Ed. 2000, 39, 739.
11. (a) Nozawa, Y.; Ito, M.; Sugawara, K.; Hanada, K.; Mizoue, K. J. Antibiotics 1997, 50, 641.
12. (b) Matsumoto, K.; Nagashima, K.; Kamigauchi, T.; Kawamura, Y.; Yasuda, Y.; Ishii, K.; Uotani, N.; Sato, T.; Nakai, H.; Terui, Y.; Kikuchi, J.; Ikenisi, Y.; Yoshida, T.; Kato, T.; Itazaki, H. J. Antibiotics 1995, 48, 439.
13. (c) Jakupovic, J.; Schuster, A.; Sun, H.; Bolman, F.; Bhakuni, D. S. Phytochemistry 1987, 26, 580.
14. (d) Kosin, J.; Ruangrungsi, N.; Ito, C.; Furukawa, H. Phytochemistry 1998, 47, 1167.
15. (e) Paramana, D.; Lajis, N. H.; Mackeen, M. M.; Ali, A. M.; Aimi, A. N.; Kitajima, M.; Takayama, H. J. Nat. Prod. 2001, 64, 976.
16. (f) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 9074.
17. (g) Daikonya, A.; Katsuki, S.; Wu, J.-B.; Kitanaka, S. Chem. Pharm. Bull. 2002, 50, 1566.
18. (h) Tahara, S.; Ibrahim, R. K. Phytochemistry 1995, 38, 1073; and references cited therein (4a-h).
19. (a) Saimoto, H.; Yoshida, K.; Murakami, T.; Morimoto, M.; Sashiwa, H.; Shigemasa, Y. J. Org. Chem. 1996, 61, 6768.
20. (b) Spyroudis, S.; Tarantill, P. Tetrahedron 1994, 50, 11541.
21. (c) Kang, Y.; Mei, Y.; Du, Y.; Jin, Z. Org. Lett. 2003, 5, 4481.
22. (a) Mali, R. S.; Babu, K. N. J. Chem. Research, Synop. 1998, 292.
23. (b) Tisdala, E. J.; Kochman, D. A.; Theodorakis, E. A. Tetrahedron Lett. 2003, 44, 3281.
24. (c) Kalena, G. P.; Jain, A.; Banerji, A. Molecules 1997, 2, 100.
25. (a) Kar, A.; Argade, N. P. Tetrahedron 2003, 59, 2991.
26. (b) Kar, A.; Argade, N. P. J. Org. Chem. 2002, 67, 7131.
27. (c) Mhaske, S. B.; Argade, N. P. J. Org. Chem. 2001, 66, 9038.
28. (d) Mangaleswaran, S.; Argade, N. P. J. Org. Chem. 2001, 66, 5259; and references cited therein (7a-d).
29. Upon silica gel column chromatographic purification of 3, only 1 was eluted from the column. Neutral alumina column purification gave only DBU.