A synthesis of D,L-N,N-dimethylcycloisodityrosines: A comment on the stereochemistry of previously reported intermediates related to the synthesis of RA-VII and deoxybouvardin

Journal of Organic Chemistry

Volumn 61, Issue 12, 1996, Pages 3936-3937

  Inoue, Tsutomu ^a   Sasaki, Tomomitsu ^a   Takayanagi, Hiroaki ^b   Harigaya, Yoshihiro ^b   Hoshino, Osamu ^c   Hara, Hiroshi ^c   Inaba, Takashi ^d  

^a Fuji Yakuhin Co Ltd   (Japan)

^b KITASATO UNIVERSITY   (Japan)

^c TOKYO UNIVERSITY OF SCIENCE   (Japan)

^d Japan Tabaco Inc   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE; DEOXYBOUVARDIN; N,N DIMETHYLCYCLOISODITYROSINE; RA VII; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0029952522     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960381s     Document Type: Article

References (18)

1. (a) Jolad, S. D.; Hoffmann, J. J.; Torrance, S. J.; Wiedhopf, R. M.; Cole, J. R.; Arora, S. K.; Bates, R. B.; Gargiulo, R. L.; Kriek, G. R. J. Am. Chem. Soc. 1977, 99, 8040.
2. (b) Bates, R. B.; Cole, J. R.; Hoffmann, J. J.; Kriek, G. R.; Linz, G. S.; Torrance, S. J. J. Am. Chem. Soc. 1983, 105, 1343.
3. (a) For a review on oligopeptides related to RA: Itokawa, H.; Takeya, K. Heterocycles 1993, 35, 1482-1501 and references cited therein,
4. (b) Itokawa, H.; Saitou, K.; Morita, H.; Takeya, K.; Yamada, K. Chem. Pharm. Bull. 1992, 40, 2984.
5. (c) Hitotsuyanagi, Y.; Suzuki, J.; Takeya, K.; Itokawa, H. Bioorg. Med. Chem. Lett. 1994, 4, 1633.
6. (d) Itokawa, H.; Kondo, K.; Hitotsuyanagi, Y.; Isomura, M.; Takeya, K. Chem. Pharm. Bull. 1993, 42, 1402.
7. (a) Inaba, T.; Umezawa, I.; Yuasa, M.; Inoue, T.; Mihashi, S.; Itokawa, H.; Ogura, K. J. Org. Chem. 1987, 52, 2957.
8. (b) Inoue, T.; Inaba, T.; Umezawa, I.; Yuasa, M.; Komatsu, K.; Itokawa, H.; Ogura, K.; Hara, H.; Hoshino, O. Chem. Pharm. Bull. 1995, 43, 1325.
9. (a) Boger, D. L; Yohannes, D. J. Am. Chem. Soc. 1991, 113, 14.
10. (b) Boger, D. L.; Yohannes, D.; Zhou, J.; Patane, M. A. J. Am. Chem. Soc. 1993, 115, 3420.
11. Boger, D. L.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7364.
12. 5 However, the origin of this discrepancy in the spectral properties had not been addressed.
13. Izumiya, N.; Nagamatsu, A. Bull. Chem. Soc. Jpn. 1952, 25, 265.
14. 5
15. 3
16. Atomic coordinates for this structure have been deposited with the Cambridge Crystallographic Data Center. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB2 1EZ, UK.
17. 12
18. Boger, D. L.; Zhou, J. J. Org. Chem. 1996, 61, XXXX.