Absolute conformation and substituent effects on chiroptical properties of 9-(2-halo-1,1-dimethylethyl)-11,12-bis(methoxycarbonyl)-9,10-dihydro-9 ,10-ethenoanthracenes

Journal of the American Chemical Society

Volumn 118, Issue 46, 1996, Pages 11460-11466

  Toyota, Shinji ^a   Akinaga, Tadashi ^a   Kojima, Hiroharu ^a   Aki, Michihiko ^a   Oki, Michinori ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACENE DERIVATIVE;

ARTICLE; CIRCULAR DICHROISM; DRUG PURIFICATION; DRUG STRUCTURE; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; X RAY ANALYSIS;

EID: 0029909514     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961520q     Document Type: Article

References (24)

1. This paper is dedicated to Professor Nelson J. Leonard on the occasion of his 80th birthday.
2. Part 5 of the series, Absolute Conformation and Chiroptical Properties. For Part 4, see Toyota, S.; Yasutomi, A.; Ōki, M. Tetrahedron Lett. 1995, 36, 6297-6300.
3. Toyota, S.; Yamane, H.; Ōki, M. Bull. Chem. Soc. Jpn. 1993, 66, 212-217.
4. Toyota, S.; Miyasaka, T.; Matsumoto, Y.; Matsuo, T.; Ōki, M. Bull. Chem. Soc. Jpn. 1994, 67, 1680-1693.
5. Isaksson, R.; Ōki, M.; Sandström, J.; Suissa, M. R.; Toyota, S. Acta Chem. Scand. 1993, 47, 570-576.
6. Yamamoto, G.; Suzuki, M.; Ōki, M. Bull. Chem. Soc. Jpn. 1983, 56, 306-313.
7. Yamamoto, G.; Nakamura, M.; Ōki, M. Bull. Chem. Soc. Jpn. 1975, 48, 2592-2596.
8. Oppolzer, W.; Chapuis, C.; Bernardinelli, G. Helv. Chim. Acta 1984, 67, 1397-1401.
9. Harada, N.; Soutome, T.; Nehira, T.; Uda, H.; Oi, S.; Okamura, A.; Miyano, S. J. Am. Chem. Soc., 1993, 115, 7547-7548. Harada, N.; Soutome, T.; Murai, S.; Uda, S. Tetrahedron Asymmetry 1993, 4, 1755-1758: Harada, N.; Hattori, T.; Suzuki, T.; Okamura, A.; Ono, H.; Miyano, S.; Uda, H. Tetrahedron Asymmetry 1993, 4, 1789-1792. Hagiwara, H.; Okamoto, T.; Hrarada, N.; Uda, H. Tetrahedron, 1995, 36, 9891-9898.
10. Harada, N.; Soutome, T.; Nehira, T.; Uda, H.; Oi, S.; Okamura, A.; Miyano, S. J. Am. Chem. Soc., 1993, 115, 7547-7548. Harada, N.; Soutome, T.; Murai, S.; Uda, S. Tetrahedron Asymmetry 1993, 4, 1755-1758: Harada, N.; Hattori, T.; Suzuki, T.; Okamura, A.; Ono, H.; Miyano, S.; Uda, H. Tetrahedron Asymmetry 1993, 4, 1789-1792. Hagiwara, H.; Okamoto, T.; Hrarada, N.; Uda, H. Tetrahedron, 1995, 36, 9891-9898.
11. Harada, N.; Soutome, T.; Nehira, T.; Uda, H.; Oi, S.; Okamura, A.; Miyano, S. J. Am. Chem. Soc., 1993, 115, 7547-7548. Harada, N.; Soutome, T.; Murai, S.; Uda, S. Tetrahedron Asymmetry 1993, 4, 1755-1758: Harada, N.; Hattori, T.; Suzuki, T.; Okamura, A.; Ono, H.; Miyano, S.; Uda, H. Tetrahedron Asymmetry 1993, 4, 1789-1792. Hagiwara, H.; Okamoto, T.; Hrarada, N.; Uda, H. Tetrahedron, 1995, 36, 9891-9898.
12. Harada, N.; Soutome, T.; Nehira, T.; Uda, H.; Oi, S.; Okamura, A.; Miyano, S. J. Am. Chem. Soc., 1993, 115, 7547-7548. Harada, N.; Soutome, T.; Murai, S.; Uda, S. Tetrahedron Asymmetry 1993, 4, 1755-1758: Harada, N.; Hattori, T.; Suzuki, T.; Okamura, A.; Ono, H.; Miyano, S.; Uda, H. Tetrahedron Asymmetry 1993, 4, 1789-1792. Hagiwara, H.; Okamoto, T.; Hrarada, N.; Uda, H. Tetrahedron, 1995, 36, 9891-9898.
13. Dalcanale, F.; Montanari, F. J. Org. Chem. 1986, 51, 567-569.
14. Oppolzer, W. Pure Appl. Chem. 1990, 62, 1241-1250.
15. Buckle, M. J. C.; Fleming, I.; Gil, S. Tetrahedron Lett. 1992, 33, 4479-4482.
16. A trade name of Daicel Co. for a chiral column.
17. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron Lett. 1983, 24, 4979-4982: Barton, D. H. R.; Lacher, B.; Zard, S. Z. Tetrahedron 1987, 43, 4321-4328.
18. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron Lett. 1983, 24, 4979-4982: Barton, D. H. R.; Lacher, B.; Zard, S. Z. Tetrahedron 1987, 43, 4321-4328.
19. Rekker, R. F.; Brombacher, P. J.; Hamann, H.; Nauta, W. Th. Recl. Trav. Chim. 1954, 73, 410-416.
20. Ōki, M.; Taguchi, Y.; Okamoto, T.; Miyasaka, T.; Hamada, K.; Toyota, S.; Yonemoto, K.; Yamamoto, G. Bull. Chem. Soc. Jpn. 1993, 66, 3790-3796.
21. Tanaka, T.; Yonemoto, K.; Nakai, Y.; Yamamoto, G.; Ōki, M. Bull. Chem. Sco. Jpn. 1988, 61, 3239-3248.
22. Towson, J. C.; Weismiller, M. C.; Lal, G. S. Org. Synth. 1990, 69, 158-168: Weismiller, M. C.; Towson, J. C.; Davis, F. A. Org. Synth. 1990, 69, 154-157.
23. Towson, J. C.; Weismiller, M. C.; Lal, G. S. Org. Synth. 1990, 69, 158-168: Weismiller, M. C.; Towson, J. C.; Davis, F. A. Org. Synth. 1990, 69, 154-157.
24. For designation of absolute conformation, see ref 3.