Stereocontrol in pinacol ring-contraction of cyclopeptidyl glycols: The diazonamide C10 problem

Angewandte Chemie - International Edition

Volumn 39, Issue 5, 2000, Pages 937-940

  Chen, Xin ^a   Esser, Lothar ^a   Harran, Patrick G ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

Asymmetric synthesis; Ligand effects; Natural products; Palladium; Rearrangements

Indexed keywords

ANTINEOPLASTIC AGENT; CYCLOPEPTIDE; DIAZONAMIDE A; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034599008     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000303)39:5<937::AID-ANIE937>3.0.CO;2-A     Document Type: Article

References (22)

1. a) N. Lindquist, W. Fenical, G. D. Van Duyne, J. Clardy, J. Am. Chem. Soc. 1991, 113, 2303-2304;
2. b) N. Lindquist, PhD thesis, University of California, San Diego (USA), 1989.
3. C. Petit, San Francisco Chronicle. Jan. 31, 1997, p. A4.
4. For alternate approaches to diazonamide synthesis, see a) H. C. Hang, E. Drotleff, G. I. Elliott, T. A. Ritsema, J. P. Konopelski, Synthesis 1999, 398-400;
5. b) P. Magnus, J. D. Kreisberg, Tetrahedron Lett. 1999, 40, 451-454;
6. c) P. Magnus, J. D. Kreisberg, Abstracts of Papers 218th National Meeting of the ACS (New Orleans, LA) 1999, ORGN 623;
7. d) A. Boto, M. Ling, G. Meek, G. Pattenden, Tetrahedron Lett. 1998, 39, 8167-8170;
8. e) P. Wipf, F. Yokokawa, Tetrahedron Lett. 1998, 39, 2223-2226;
9. f) T. F. Jamison, PhD thesis, Harvard University (USA), 1997;
10. g) C. J. Moody, K. J. Doyle, M. C. Elliott, T. J. Mowlem, J. Chem. Soc. Perkin Trans. I 1997, 2413-2419;
11. h) J. Wang, PhD thesis, University of Wisconsin-Madison (LISA), 1997;
12. i) E. Vedejs, J. Wang, Abstracts of Papers 212th National Meeting of the ACS (Orlando, FL), 1996, ORGN 93;
13. j) J. P. Konopelski, J. M. Hottenroth, H. M. Oltra, E. A. Véliz, Z. C. Yang, Synlett 1996, 609-611;
14. k) C. J. Moody, K. J. Doyle, M. C. Elliott, T. J. Mowlem, Pure Appl. Chem. 1994, 66, 2107-2110.
15. S. Jeong, X. Chen, P. G. Harran, J. Org. Chem. 1998, 63, 8640-8641.
16. a) K. Nakamura, Y. Osamura, Tetrahedron Lett. 1990, 31, 251-254;
17. b) D. J. Cram, J. Am. Chem. Soc. 1949, 71, 3863-3870.
18. A. Aranyos, D. W. Old, A. Kiyomori, J. P. Wolfe, J. P. Sadighi, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 4369-4378.
19. F. He, Y. Bo, J. D. Altom, E. J. Corey, J. Am. Chem. Soc. 1999, 121, 6771-6772.
20. G. B. Feigelson, M. Egbertson, S. J. Danishefsky, G. Schulte, J. Org. Chem. 1988, 53, 3391-3393.
21. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-135208, CCDC-135152, and CCDC-135051. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: ( + 44)1223-336-1133: e-mail: deposit@ccdc.cam.ac.uk).
22. 3. See A. Basha, M. Lipton, S. M. Weinreb, Tetrahedron Lett. 1977, 4171-4174.