Synthesis of (+),(-)-model compounds and absolute configuration of carthamin; A red pigment in the flower petals of safflower

Chemistry Letters

Volumn , Issue 10, 1996, Pages 833-834

  Sato, Shingo ^a   Obara, Heitaro ^a   Kumazawa, Toshihiro ^a   Onodera, Jun Ichi ^a   Furuhata, Kimio ^b  

^a YAMAGATA UNIVERSITY   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030355155     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.833     Document Type: Article

References (17)

1. Preiser, J. Pr. Chem., [i]32, 142(1844). C. Kuroda, Nippon Kagaku Kaishi, 51, 237(1930). C. Kuroda, J. Chem. Soc., 1930, 752, T. R. Seshadri and R. S. Thakur, Curr. Sci., 29(2), 54(1960).
2. Preiser, J. Pr. Chem., [i]32, 142(1844). C. Kuroda, Nippon Kagaku Kaishi, 51, 237(1930). C. Kuroda, J. Chem. Soc., 1930, 752, T. R. Seshadri and R. S. Thakur, Curr. Sci., 29(2), 54(1960).
3. Preiser, J. Pr. Chem., [i]32, 142(1844). C. Kuroda, Nippon Kagaku Kaishi, 51, 237(1930). C. Kuroda, J. Chem. Soc., 1930, 752, T. R. Seshadri and R. S. Thakur, Curr. Sci., 29(2), 54(1960).
4. Preiser, J. Pr. Chem., [i]32, 142(1844). C. Kuroda, Nippon Kagaku Kaishi, 51, 237(1930). C. Kuroda, J. Chem. Soc., 1930, 752, T. R. Seshadri and R. S. Thakur, Curr. Sci., 29(2), 54(1960).
5. H. Obara and J. Onodera, Chem. Lett., 1979, 201. J. Onodera, T Saito, and H. Obara, Chem. Lett., 1979, 1327
6. H. Obara and J. Onodera, Chem. Lett., 1979, 201. J. Onodera, T Saito, and H. Obara, Chem. Lett., 1979, 1327
7. An adequate crystal for X-ray analysis has not been obtained hitherto.
8. 5a
9. a) H. Obara, S. Namai, and Y. Machida, Chem. Lett., 1986, 495.
10. b) H. Obara, J. Onodera, and F. Shirasaki, Chem. Lett., 1980, 1095.
11. 6) δ=208.8, 203.0, 198.3, 179.6, 162.0, 148.6, 132.0, 125.1, 116.4, 113.6, 108.1, 85.1, 45.0, 25.9. (formula presented)
12. 6) δ=208.8, 203.0, 198.3, 179.6, 162.0, 148.6, 132.0, 125.1, 116.4, 113.6, 108.1, 85.1, 45.0, 25.9. (formula presented)
13. 6) δ=208.8, 203.0, 198.3, 179.6, 162.0, 148.6, 132.0, 125.1, 116.4, 113.6, 108.1, 85.1, 45.0, 25.9. (formula presented)
14. 3 × 2), 6.86 and 7.75(each 4H, d, J=8.5 Hz, p-substituted PhH × 8), 7.75 and 7.96(each 2H, d, J=15.8 Hz, trans-vinyl H × 4), 8.39 (1H, s, =CH-), 10.14(2H, s, OH × 2), 19.40(2H, br.s, chelated OH × 2). HR-FAB/LSI MS(-): 613.1325, Calcd. 613.1346.
15. 3), 3.93(1H, d, J=9.2 Hz, H-1′), 4.02(1H, dd, J=4.9 and 12.4 Hz, H-6′a), 4.09(1H, dd, J= 2.7 and 12.4 Hz, H-6′b), 4.94(1H, t, J=9.2 Hz, H-4′), 5.14(1H, t, J=9.2 Hz, H-3′), 5.21(1H, t, J=9.2 Hz, H-2′), 5.43(1H, s, olefinic H), 18.15 (1H, s, chelated OH). (formula presented) The synthesis of 10 will be reported elsewhere.
16. 2 carbon.
17. 3) δ=1.02(3H, s. Me), 1.13(3H, s. Me), 1.17(3H, s, Me), 1.64(3H, s, Me), 2.57(3H, s, COMe), 3.83(3H, s, OMe), 5.49(1H, s, olefinic H), 18.47(1H, s, chelated OH).