Synthesis of (9S,12S)-cycloisodityrosine and its unnatural (9R,12S)-diastereomer

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 10, 1996, Pages 1089-1092

  Boger, Dale L ^a   Zhou, Jiacheng ^a   Borzilleri, Robert M ^a   Nukui, Seiji ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONIC ACID DERIVATIVE; DIAZONIUM COMPOUND; ETHER DERIVATIVE; METHYL CHLORIDE; N,N DIMETHYLFORMAMIDE; PIPERAZINE DERIVATIVE; TYROSINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; CRYSTAL STRUCTURE; CYCLIZATION; DERIVATIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; MOLECULAR INTERACTION; X RAY CRYSTALLOGRAPHY;

EID: 0029995528     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00179-5     Document Type: Article

References (17)

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3. 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. Review: Itokawa, H.; Takeya, K. Heterocycles 1993, 35, 1467. Itokawa, H.; Takeya, K.; Mori, N.; Sonobe, T.; Mihashi, S.; Hamanaka, T. Chem. Pharm. Bull. 1986, 34, 3762. Itokawa, H.; Takeya, K.; Mihara, K.; Mon, N.; Hamanaka, T.; Sonobe, T.; Iitaka, Y. Chem. Pharm. Bull. 1983, 31, 1424.
4. 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. Review: Itokawa, H.; Takeya, K. Heterocycles 1993, 35, 1467. Itokawa, H.; Takeya, K.; Mori, N.; Sonobe, T.; Mihashi, S.; Hamanaka, T. Chem. Pharm. Bull. 1986, 34, 3762. Itokawa, H.; Takeya, K.; Mihara, K.; Mon, N.; Hamanaka, T.; Sonobe, T.; Iitaka, Y. Chem. Pharm. Bull. 1983, 31, 1424.
5. 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. Review: Itokawa, H.; Takeya, K. Heterocycles 1993, 35, 1467. Itokawa, H.; Takeya, K.; Mori, N.; Sonobe, T.; Mihashi, S.; Hamanaka, T. Chem. Pharm. Bull. 1986, 34, 3762. Itokawa, H.; Takeya, K.; Mihara, K.; Mon, N.; Hamanaka, T.; Sonobe, T.; Iitaka, Y. Chem. Pharm. Bull. 1983, 31, 1424.
6. Boger, D. L.; Zhou, J. J. Am. Chem. Soc. 1993, 115, 11426.
7. Boger, D. L.; Zhou, J. J. Org. Chem. in press.
8. Beugelmans, R.; Bigot, A.; Bois-Choussy, M.; Zhu, J. J. Org. Chem. 1996, 61, 771.
9. 2, 25 °C, 3 h, 87%).
10. 3) for (S,S)-3.
11. 5 but represented as thermally stable, noninterconvertable atropisomers. The report that the starting materials and products are stable to base and the macrocyclization conditions are not accurate and our independent efforts establish that the two diastereomers are related by C9 epimerization.
12. 7 (HOBt-EDCI, C12 center) in addition to that which occurs upon macrocyclization (C9 center).
13. The atomic coordinates for this structure have been deposited with the Cambridge Crystallographic Data Centre and may be obtained from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
14. 12 requires their reassignment to the diastereomer 13-14 stereochemistry. The ramifications of these reassignments are under investigation and will be disclosed in due time.
15. Boger, D. L.; Patane, M. A.; Jin, Q.; Kitos, P. A. Bioorg. Med Chem. 1994, 2, 85. Boger, D. L.; Zhou, J. Bioorg. Med. Chem. 1995, 3, 1579. Boger, D. L.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7364.
16. Boger, D. L.; Patane, M. A.; Jin, Q.; Kitos, P. A. Bioorg. Med Chem. 1994, 2, 85. Boger, D. L.; Zhou, J. Bioorg. Med. Chem. 1995, 3, 1579. Boger, D. L.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7364.
17. Boger, D. L.; Patane, M. A.; Jin, Q.; Kitos, P. A. Bioorg. Med Chem. 1994, 2, 85. Boger, D. L.; Zhou, J. Bioorg. Med. Chem. 1995, 3, 1579. Boger, D. L.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7364.