Stereochemical assignments for all four isomers of dolaproine via lactam formation

Synthesis

Volumn , Issue 24, 2007, Pages 3846-3850

  Shang, Xiao ^a   Nguyen, Minh ^a   Ihle, Nathan C ^a  

^a SEATTLE GENETICS INC   (United States)

Author keywords

Aldol reaction; Auristatin; Coupling constant; Dolaproine; Dolastatin; Lactam; NOE; Stereochemical

Indexed keywords

ALDOL REACTIONS; BICYCLIC LACTAMS; COUPLING CONSTANTS; DOLAPROINE; LACTAM FORMATION; STEREOISOMERS;

REACTION KINETICS; SPECTRUM ANALYSIS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ISOMERS;

ANTINEOPLASTIC AGENT; AURISTATIN; DOLAPROINE; DOLASTATIN; LACTAM; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 37549057307     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990936     Document Type: Article

References (20)

1. (a) Pettit, G. R.; Kamano, Y.; Herald, C. L.; Tuinman, A. A.; Boettner, F. E.; Kizu, H.; Schmidt, J. M.; Baczynskyj, L. J. Am. Chem. Soc. 1987, 109, 6883.
2. (b) Madden, T.; Tran, H. T.; Beck, D.; Huie, R.; Newman, R. A.; Pusztai, L.; Wright, J. J.; Abbruzzese, J. L. J. Clin. Oncol. 2000, 6, 1293.
3. (a) Doronina, S. O.; Toki, B. E.; Torgov, M. T.; Mendelsohn, B. A.; Cerveny, C. G.; Chace, D. F.; DeBlanc, R. L.; Gearing, R. P.; Bovee, T. D.; Siegall, C. B.; Francisco, J. A.; Wahl, A. F.; Meyer, D. L.; Senter, P. D. Nature Biotechnol. 2003, 21, 778.
4. (b) Doronina, S. O.; Mendelsohn, B. A.; Bovee, T. D.; Cerveny, C. G.; Alley, S. C.; Meyer, D. L.; Oflazoglu, E.; Toki, B. E.; Sanderson, R. J.; Zabinski, R. F.; Wahl, A. F.; Senter, P. D. Bioconjugate Chem. 2006, 17, 114.
5. (a) Pettit, G. R.; Singh, S. B.; Hogan, F.; Lloyd-Williams, P.; Herald, D. L.; Burkett, D. D.; Clewlow, P. J. J. Am. Chem. Soc. 1989, 111, 5463.
6. (b) Pettit, G. R.; Barkóczy, J.; Srirangam, J. K.; Singh, S. B.; Herald, D. L.; Williams, M. D.; Kantoci, D.; Hogan, F.; Groy, T. L. J. Org. Chem. 1994, 59, 2935.
7. (c) Pettit, G. R.; Srirangam, J. K.; Herald, D. L.; Hamel, E. J. Org. Chem. 1994, 59, 6127.
8. (a) Hamada, Y.; Hayashi, S.; Shioiri, T. Tetrahedron Lett. 1991, 32, 931.
9. (b) Hayashi, K.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1991, 32, 7287.
10. (c) Tomioka, K.; Kanai, M.; Koga, K. Tetrahedron Lett. 1991, 32, 2395.
11. (d) Roux, F.; Maugras, I.; Poncet, J.; Niel, G.; Jouin, P. Tetrahedron 1994, 50, 5345.
12. (e) Pettit, G. R.; Grealish, M. P. J. Org. Chem. 2001, 66, 8640.
13. (f) Almeida, W.; Coelho, F. Tetrahedron Lett. 2003, 44, 937.
14. (a) Mordant, C.; Reymond, S.; Ratovelomanana-Vidal, V.; Genet, J.-P. Tetrahedron 2004, 60, 9715.
15. (b) Lavergne, D.; Mordant, C.; Ratovelomanana-Vidal, V.; Genet, J.-P. Org. Lett. 2001, 3, 1909.
16. Pettit, G. R.; Singh, S. B.; Herald, D. L.; Lloyd-Williams, P.; Kantoci, D.; Burkett, D. D.; Barkoczy, J.; Hogan, F.; Warlaw, T. R. J. Org. Chem. 1994, 59, 6287.
17. Chem 3D, version 9.0, from CambridgeSoft, and Spartan, version 1.01, from Wavefunctions Inc.
18. (a) See: http://www.casper.organ.su.se/ke3690/jhh.html (accessed 9 November 2007).
19. (b) Pretsch, E.; Buhlmann, P.; Affolter, C. Structure Determination of Organic Compounds, 3rd ed.; Springer: Berlin, 2000, 167.
20. (c) Karplus, M. J. Am. Chem. Soc. 1963, 85, 2870.