The asymmetric total synthesis of (+)- and (-)-spirotryprostatin B [16]

Journal of the American Chemical Society

Volumn 122, Issue 23, 2000, Pages 5666-5667

  Sebahar, Paul R ^a   Williams, Robert M ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMITOTIC AGENT; CYCLOTRYPROSTATIN; SPIROTRYPROSTATIN B; TRYPOSTATIN; UNCLASSIFIED DRUG;

CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; LETTER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034647225     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001133n     Document Type: Letter

References (33)

1. (a) Cui, C. B.; Kakeya, H.; Osada, H. J. Antibiot. 1996, 49, 832-835.
2. (b) Cui, C. B.; Kakeya, H.; Osada, H. Tetrahedron 1996, 51, 12651-12666.
3. Cui, C. B.; Kakeya, H.; Osada, H. Tetrahedron. 1997, 53, 59-72.
4. (a) Cui, C. B.; Kakeya, H.; Okada, G.; Ubukata, M.; Takahashi, I.; Isono, K.; Osada, H. J. Antibiot. 1995, 48, 1382-1384.
5. (b) Cui, C. B.; Kakeya, H.; Okada, G.; Onose, R.; Osada, H. J. Antibiot. 1996, 49, 527-533.
6. (c) Cui, C. B.; Kakeya, H.; Osada, H. J. Antibiot. 1996, 49, 534-540.
7. (a) Usui, T.; Kondoh, M.; Cui, C. B.; Mayumi, T.; Osada, H. Biochem. J. 1998, 333, 543.
8. (b) Kondoh, M.; Usui, T.; Cui, C. B.; Mayumi, T.; Osada, H. J. Antibiot. 1998, 51, 801-804.
9. For a review, see: Williams, R. M.; Sanz-Cervera, J. F.; Stocking, E. In Topics in Current Chemistry, Volume on Biosynthesis-Terpenes and Alkaloids; Leeper, F., Vederas, J. C., Eds.; Springer-Verlag: Duesseldorf, Germany, 2000; Vol. 209, pp 97-173.
10. (a) Edmonson, S. D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 1998, 37, 1138-1140.
11. (b) Edmonson, S. D.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 2147-2155.
12. For an entirely different approach to spirotryprostatin B, see: (c) Overman, L. E.; Rosen, M. D.; Osada, H.; Shaka, A. J.; Taylor, N. D. Abstracts of the ACS National Meeting, San Francisco, March 26-30, 2000; American Chemical Society: Washington, DC;Abstract No. 843.
13. For a recent review, see: Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 863-909.
14. Williams, R. M.; Zhai, W.; Aldous, D. J.; Aldous, S. C. J. Org. Chem. 1992, 57, 6527-6532.
15. (a) Grigg, R.; Basanagoudar, L. D.; Kennedy, D. A.; Malone, J. F.; Thianpatanagul, S. Tetrahedron Lett. 1982, 23, 2803-2806.
16. (b) Grigg, R.; Aly, M. F.; Seidharan, V.; Thianpatanagul, S. J. Chem. Soc., Chem. Commun. 1984, 182-183.
17. (c) Wenkert, E.; Liu, S. Synthesis 1992, 323-327.
18. (d) Casaschi, A.; Faita, G.; Gamba Invernizzi, A.; Grunanger, P. Gazz. Chim. Ital. 1993, 123, 137-143.
19. (d) Palmisano, G.; Annunziata, R.; Papeo, G.; Sisti, M. Tetrahedron Asymm. 1996, 7, 1-4.
20. (e) Nyerges, M.; Gajdics, L.; Szollosy, A.; Toke, L. Synth. Lett. 1999, 111-113.
21. (f) Grigg, R.; Landsell, M. I.; Thorton-Pett, M. Tetrahedron, 1999, 55, 2025-2044.
22. (g) Fejes, I.; Toke, L.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 639-644.
23. Aldehyde 8 is obtained from inexpensive, commercially available 3-methoxy-3-methyl-1-butanol (Aldrich Chemical Co.) by Swern oxidation in 89% yield.
24. 2Et in refluxing diglyme in 84% yield.
25. "β" refers to the approach of the dipolarophile from the top face as drawn in Scheme 2.
26. The yield for the conversion of 12 to the L-proline isomer corresponding to 13 was 52% and this diminished yield appears to reflect the thermodynamic instability of forming the corresponding trans-diketopiperazine.
27. (a) Elsinger, F.; Schreiber, J.; Eschenmoser, A. Helv. Chim. Acta 1960, 43, 113-117.
28. (b) Borch, R. F.; Grudzinskas, C. V.; Peterson, D. A.; Weber, L. D. J. Org. Chem. 1972, 37, 1141-1145.
29. 4 used in the total synthesis of natural products see: (a) Patel, D. V.; VanMiddlesworth, F.; Donubauer, J.; Gannett, P.; Sih, C. J. J. Am. Chem. Soc. 1986, 108, 4603-4614.
30. (b) Sternbach, D. D.; Hughes, J. W.; Burdi, D. F.; Banks, B. A. J. Am. Chem. Soc. 1985, 107, 2149-2153.
31. Concepcion, J. I.; Francisco, C. G.; Friere, R.; Hernandez, R.; Slazar, J. A.; Suarez, E. J. J. Org. Chem. 1986, 51, 402.
32. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901.
33. Since submission of our paper, we have learned that Profs. Overman and Danishefsky have also independently achieved the synthesis of spirotryprostatin B; we thank both Profs. Danishefsky and Overman for making us aware of their work prior to publication.