Alternative synthesis of the cycloisodityrosine subunit of deoxybouvardin, RA-VII, and related agents: Reassignment of the stereochemistry of prior intermediates

Journal of Organic Chemistry

Volumn 61, Issue 12, 1996, Pages 3938-3939

  Boger, Dale L ^a   Zhou, Jiacheng ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOISODITYROSINE; CYCLOPEPTIDE; DEOXYBOUVARDIN; RA VII; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029941267     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9604144     Document Type: Article

References (36)

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16. 3).
17. 2, 25 0C, 74-83%).
18. Extensive racemization is observed if the N-methylation of BOC-Tyr(OBn)-OH is conducted on a corresponding ester or under conditions where the methyl ester is formed directly especially if excess NaH is employed,
19. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates may be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
20. Boger, D. L.; Yohannes, D. Tetrahedron Lett. 1989, 30, 2053. Boger, D. L.; Yohannes, D. J. Org. Chem. 1991, 56, 1763. Boger, D. L.; Nomoto, Y.; Teegarden, B. R. J. Org. Chem. 1993, 58, 1425. Boger, D. L.; Yohannes, D. J. Org. Chem. 1989, 54, 2498. Boger, D. L.; Yohannes, D. Tetrahedron Lett. 1989, 30, 5061. Boger, D. L.; Yohannes, D. J. Org. Chem. 1990, 55, 6000.
21. Boger, D. L.; Yohannes, D. Tetrahedron Lett. 1989, 30, 2053. Boger, D. L.; Yohannes, D. J. Org. Chem. 1991, 56, 1763. Boger, D. L.; Nomoto, Y.; Teegarden, B. R. J. Org. Chem. 1993, 58, 1425. Boger, D. L.; Yohannes, D. J. Org. Chem. 1989, 54, 2498. Boger, D. L.; Yohannes, D. Tetrahedron Lett. 1989, 30, 5061. Boger, D. L.; Yohannes, D. J. Org. Chem. 1990, 55, 6000.
22. Boger, D. L.; Yohannes, D. Tetrahedron Lett. 1989, 30, 2053. Boger, D. L.; Yohannes, D. J. Org. Chem. 1991, 56, 1763. Boger, D. L.; Nomoto, Y.; Teegarden, B. R. J. Org. Chem. 1993, 58, 1425. Boger, D. L.; Yohannes, D. J. Org. Chem. 1989, 54, 2498. Boger, D. L.; Yohannes, D. Tetrahedron Lett. 1989, 30, 5061. Boger, D. L.; Yohannes, D. J. Org. Chem. 1990, 55, 6000.
23. Boger, D. L.; Yohannes, D. Tetrahedron Lett. 1989, 30, 2053. Boger, D. L.; Yohannes, D. J. Org. Chem. 1991, 56, 1763. Boger, D. L.; Nomoto, Y.; Teegarden, B. R. J. Org. Chem. 1993, 58, 1425. Boger, D. L.; Yohannes, D. J. Org. Chem. 1989, 54, 2498. Boger, D. L.; Yohannes, D. Tetrahedron Lett. 1989, 30, 5061. Boger, D. L.; Yohannes, D. J. Org. Chem. 1990, 55, 6000.
24. Boger, D. L.; Yohannes, D. Tetrahedron Lett. 1989, 30, 2053. Boger, D. L.; Yohannes, D. J. Org. Chem. 1991, 56, 1763. Boger, D. L.; Nomoto, Y.; Teegarden, B. R. J. Org. Chem. 1993, 58, 1425. Boger, D. L.; Yohannes, D. J. Org. Chem. 1989, 54, 2498. Boger, D. L.; Yohannes, D. Tetrahedron Lett. 1989, 30, 5061. Boger, D. L.; Yohannes, D. J. Org. Chem. 1990, 55, 6000.
25. Boger, D. L.; Yohannes, D. Tetrahedron Lett. 1989, 30, 2053. Boger, D. L.; Yohannes, D. J. Org. Chem. 1991, 56, 1763. Boger, D. L.; Nomoto, Y.; Teegarden, B. R. J. Org. Chem. 1993, 58, 1425. Boger, D. L.; Yohannes, D. J. Org. Chem. 1989, 54, 2498. Boger, D. L.; Yohannes, D. Tetrahedron Lett. 1989, 30, 5061. Boger, D. L.; Yohannes, D. J. Org. Chem. 1990, 55, 6000.
26. Similar, but unrecognized, observations have been recently disclosed. Beugelmans, R.; Bigot, A.; Bois-Choussy, M.; Zhu, J. J. Org. Chem. 1996, 61, 771.
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31. Boger, D. L.; Yohannes, D.; Myers, J. B. J. Org. Chem. 1992, 57, 1319. 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. Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7357. Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544.
32. Boger, D. L.; Yohannes, D.; Myers, J. B. J. Org. Chem. 1992, 57, 1319. 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. Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7357. Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544.
33. Boger, D. L.; Yohannes, D.; Myers, J. B. J. Org. Chem. 1992, 57, 1319. 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. Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7357. Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544.
34. Boger, D. L.; Yohannes, D.; Myers, J. B. J. Org. Chem. 1992, 57, 1319. 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. Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7357. Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544.
35. Boger, D. L.; Yohannes, D.; Myers, J. B. J. Org. Chem. 1992, 57, 1319. 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. Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7357. Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544.
36. Boger, D. L.; Yohannes, D.; Myers, J. B. J. Org. Chem. 1992, 57, 1319. 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. Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7357. Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544.