Efficient synthesis of analogs of safflower yellow B, carthamin, and its precursor: Two yellow and one red dimeric pigments in safflower petals

Tetrahedron

Volumn 61, Issue 40, 2005, Pages 9630-9636

  Sato, Shingo ^a   Kusakari, Takashi ^a   Suda, Tohru ^a   Kasai, Takaharu ^a   Kumazawa, Toshihiro ^a   Onodera, Jun Ichi ^a   Obara, Heitaro ^a  

^a YAMAGATA UNIVERSITY   (Japan)

Author keywords

(p Hydroxycinnamoyl)filicinic acid; Analog; Carthamin; Carthamin precursor; Safflower petals; Safflower yellow B; Yellow and red pigments

Indexed keywords

(4 HYDROXYCINNAMOYL)FILICINIC ACID; 2,2 BIS[3(4 HYDROXYCINNAMOYL)FILINIC ACID 5 YL]ACETIC ACID; 2,3,4,5,6 PENTA O ACETYL ALDEHYDRO DEXTRO GLUCOSE; CARTHAMIN; CARTHAMUS TINCTRIOUS EXTRACT; FORMIC ACID DERIVATIVE; GLYOXYLIC ACID; PERMANGANATE POTASSIUM; PHLOROGLUCINOL; PIGMENT; PLANT EXTRACT; SAFFLOWER YELLOW B; TRIETHYL ORTHOFORMATE; UNCLASSIFIED DRUG;

ARTICLE; DECARBOXYLATION; DIMERIZATION; NONHUMAN; PETAL; PRECURSOR; PRIORITY JOURNAL; SAFFLOWER; STRUCTURE ANALYSIS; SYNTHESIS;

CARTHAMUS; CARTHAMUS TINCTORIUS;

EID: 27744449794     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.07.080     Document Type: Article

References (27)

1. (a) Obara, H.; Onodera, J.-I. Chem. Lett. 1979, 201-204.
2. (b) Takahashi, Y.; Miyasaka, N.; Tasaka, S.; Miura, I.; Urano, S.; Ikura, M.; Hikichi, K.; Matsumoto, T.; Wada, M. Tetrahedron Lett. 1982, 23, 5163-5166.
3. (a) Onodera, J.-I.; Obara, H.; Osone, M.; Maruyama, Y.; Sato, S. Chem. Lett. 1981, 433-436.
4. (b) Goda, Y.; Suzuki, J.; Kametani, T. Jpn. J. Food Chem. 1997, 4, 54-58.
5. Takahashi, Y.; Saito, K.; Yanagiya, M.; Ikura, M.; Hikichi, K.; Matsumoto, T.; Wada, M. Tetrahedron Lett. 1984, 25, 2471-2474.
6. Onodera, J.-I.; Obara, H.; Hirose, R.; Matsuba, S.; Sato, N.; Sato, S.; Suzuki, M. Chem. Lett. 1989, 1571-1574.
7. (a) Kumazawa, T.; Sato, S.; Kanenari, D.; Kunimatsu, A.; Hirose, R.; Matsuba, S.; Obara, H.; Suzuki, M.; Sato, M.; Onodera, J.-I. Chem. Lett. 1994, 2343-2344.
8. (b) Kazuma, K.; Shirai, E.; Wada, M.; Umeo, K.; Sato, A.; Matsumoto, T.; Okuno, T. Biosci. Biotechol. Biochem. 1995, 59, 1588-1590.
9. Meselhy, M. R.; Kadota, S.; Momose, Y.; Hattori, M.; Namba, T. Chem. Pharm. Bull. 1992, 40, 3355-3357.
10. Yin, H.-B.; He, Z.-S. Tetrahedron Lett. 2000, 41, 1955-1958.
11. (a) Onodera, J.-I.; Kawamoto, K.; Matsuba, S.; Sato, S.; Kojima, H.; Kaneya, Y.; Obara, H. Chem. Lett. 1995, 901-902.
12. (b) Kazuma, K.; Takahashi, T.; Sato, K.; Takeuchi, H.; Matsilmoto, T.; Okuno, T. Biosci. Biotechnol. Biochem. 2000, 64, 1588-1599.
13. (c) Meselhy, M. R.; Kadota, S.; Hattor, M.; Namba, T. J. Nat. Prod. 1993, 56, 39-45.
14. Sato, S.; Kumazawa, T.; Watanabe, H.; Takayanagi, K.; Matsuba, S.; Onodera, J.-I.; Obara, H.; Furuhata, K. Chem. Lett. 2001, 1318-1319.
15. Sato, S.; Obara, H.; Kumazawa, T.; Onodera, J.-I.; Furuhata, K. Chem. Lett. 1996, 833-834.
16. (a) Obara, H.; Machida, Y.; Namai, S.; Onodera, J.-I. Chem. Lett. 1985, 1393-1394.
17. (b) Sato, S.; Obara, H.; Onodera, J.-I.; Endo, A.; Matsuba, S. Bull. Chem. Soc. Jpn. 1992, 65, 452-457.
18. (c) Obara, H.; Onodera, J.-I.; Shirasaki, F. Chem. Lett. 1980, 1095-1098.
19. (d) Obara, H.; Namai, S.; Machida, Y. Chem. Lett. 1986, 495-496.
20. (e) Kumazawa, T.; Amano, Y.; Haga, T.; Matsuba, S.; Sato, S.; Kawamoto, K.; Onodera, J.-I. Chem. Lett. 1995, 625-626.
21. Sato, S.; Obara, H.; Endo, A.; Onodera, J.-I.; Matsuba, S. Bull. Chem. Soc. Jpn. 1992, 65, 2552-2554.
22. Campbell, T. W.; Coppinger, G. M. J. Am. Chem. Soc. 1951, 73, 2708.
23. Hoefer, K.; Riedl, W. Annalen 1962, 656, 127-130.
24. Riedl, W.; Risse, K. H. Annalen 1954, 585, 209-219.
25. Nilsson, M. Acta Chem. Scand. 1959, 13, 750.
26. Wolfrom, M. L. J. Am. Chem. Soc. 1929, 51, 2188-2193.
27. Fischer, E. Chem. Ber. 1894, 27, 673-679.