Second generation synthesis of C27 - C35 Building block of E7389, a synthetic halichondrin analogue

Organic Letters

Volumn 11, Issue 20, 2009, Pages 4516-4519

  Yang, Yu Rong ^a   Kim, Dae Shik ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (3 AMINO 2 HYDROXYPROPYL)HEXACOSAHYDRO 3 METHOXY 26 METHYL 20,27 BIS(METHYLENE)11,15 18,21 24,28 TRIEPOXY 7,9 ETHANO 12,15 METHANO 9H,15H FURO(3,2 I)FURO(2',3' 5,6)PYRANO(4,3 B)(1,4)DIOXACYCLOPENTACOSIN 5 (4H) ONE; 2-(3-AMINO-2-HYDROXYPROPYL)HEXACOSAHYDRO-3-METHOXY-26-METHYL-20,27-BIS(METHYLENE)11,15-18,21-24,28-TRIEPOXY-7,9-ETHANO-12,15-METHANO-9H,15H-FURO(3,2-I)FURO(2',3'-5,6)PYRANO(4,3-B)(1,4)DIOXACYCLOPENTACOSIN-5-(4H)-ONE; ANTINEOPLASTIC AGENT; CARBON; ETHER DERIVATIVE; FURAN DERIVATIVE; HALICHONDRIN B; KETONE; LACTONE;

ARTICLE; CHEMISTRY; SYNTHESIS;

ANTINEOPLASTIC AGENTS; CARBON; ETHERS, CYCLIC; FURANS; KETONES; LACTONES;

EID: 70349913892     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9016589     Document Type: Article

References (44)

1. For the isolation of the halichondrins from a marine sponge Halichondria okadai Kadota. see: (a) Uemura, D.; Takahashi. K.; Yamamoto, T.; Katayama, C.; Tanaka. J.: Okumura, Y.; Hirata, Y. J. Am. Chem. Soc. 1985, 107, 4796.
2. (b) Hirata, Y.: Uemura, D. Pure Appl. Chem. 1986, 58, 701. For isolation of the halichondrins from different species of sponges,
3. see: (c) Pettit, G. R.: Herald. C. L.; Boyd, M. R.; Leet, J. E.; Dufresne, C.; Doubek, D. L.: Schmidt, J. M.: Cemy, R. J.; Hooper, J. N. A.; Rützler, K. C. J. Med. Chem. 1991, 34, 3339.
4. (d) Pettit, G. R.; Tan, R.; Gao, F.; Williams, M. D.; Doubek, D. L.; Boyd, M. R.; Schmidt, J. M.: Chapuis, J.-C.: Hamel, E.: Bai, R.; Hooper, J. N. A.: Tackett, L. P. J. Org. Chem. 1993. 58, 2538.
5. (e) Litaudon, M.; Hart, J. B.: Blunt, J. W.; Lake, R. J.; Munro. M. H. G. Tsirahedron Lett. 1994, 35. 9435.
6. (f) Litaudon, M.; Hickford. S. J. H.; Lill. R. E.; Lake, R. J.: Blunt, J. W.: Munro, M. H. G. J. Org. Chem. 1997, 62. 1868.
7. (g) Hickford, S. J. H.; Blunt, J. W.: Munro, M. H. G. Bioorg. Med. Chem. 2009, 17, 2199.
8. For the synthetic work on the marine natural product halichondrins from this laboratory, see: (a) Aicher, T. D.; Buszek, K. R.; Fang, F. G.: Forsvth, C. J.; Jung, S. H.: Kishi, Y.: Matelich, M. C.; Scola, P. M.: Spero, D. M.; Yoon, S. K. J. Am. Chem. Soc. 1992. 114. 3162.
9. (b) Stamos. D. P.; Chen. S. S.; Kishi, Y. J. Org. Chem. 1997, 62, 7552.
10. (c) Choi, H.-W.: Demeke. D.; Kang, F. A.: Kishi. Y.; Nakajima, K.: Nowak, P.; Wan, Z.K.: Xie. C. Pure Appl. Chem. 2003, 75. 1.
11. (d) Namba. K.: Jun. H.-S.: Kishi. Y. J. Am. Chem. Soc. 2004, 126. 7770.
12. (e) Namba, K.; Kishi, Y. J. Am. Chem. Soc. 2005, 127. 15382.
13. (f) Kaburagi, Y.: Kishi, Y. Org. Lett. 2007. 9. 111.
14. (g) Zhang. Z.; Huang. J.; Ma. B.: Kishi, Y. Org. Lett. 2008, 10, 3073.
15. (h) Chen, C.-L.; Namba, K.; Kishi, Y. Org. Lett. 2009, 11, 409, and references cited therein.
16. For synthetic work by Salomon. Burke. Yonemitsu. and Phillips, see: (a) Kim, S.; Salomon, R. G. Tetrahedron Lett. 1989, 30. 6279.
17. Cooper, A. J.; Pan, W.; Salomon, R. G. Tetrahedron Lett. 1993. 34. 8193, and references cited therein.
18. (b) Burke, S. D.; Buckanan, J. L.; Rovin. J. D. Tetrahedron Lett. 1991. 32, 3961.
19. Lambert, W. R.: Hanson, G. H.; Benayoud, F.: Burke. S. D. J. Org. Chem. 2005, 70, 9382. and references cited therein.
20. (c) Horita. K.; Hachiya, S.: Nagasawa, M.: Hikota, M.: Yonemitsu, O. Synlett 1994, 38.
21. Horita. K.; Nishibe, S.; Yonemitsu, O. PhytochemPhytopharm. 2000, 386, and references cited therein.
22. (d) Henderson, J. A.; Jackson, K. L.: Phillips, A. J. Org. Lett. 2007, 9, 5299.
23. Jackson. K. L.: Henderson, J. A.; Motoyoshi, H.; Phillips, A. J. Angew. Chem., Int. Ed. 2009, 48, 2346, and references cited therein.
24. Kishi. Y.; Fang, F. G.; Forsyth, C. J.: Scola. P. M.: Yoon, S. K. U.S. Patent 5338866 and International Patent WO93/17650.
25. (a) Zheng, W.: Seletsky, B. M.: Palme, M. H.: Lydon. P. J.; Singer, L. A.: Chase. C. E.; Lemelin, C. A.: Shen, Y.; Davis, H.; Tremblay, L.: Towle, M. J.; Salvato. K. A.; Weis, B. F.; Aalfs, K. K.; Kishi, Y.; Littlefield, B. A.; Yu, M. Bioorg. Med. Chem. Lett. 2004, 14, 5551.
26. (b) Littlefield, B. A.: Palme, M. H.: Seletsky, B. M.: Towle, M. J.; Yu, M. J.; Zheng. W. U.S. Patents 6214865, 6365759, and International Patent W099/65894.
27. (c) Yu, M. J.; Kishi, Y.; Littlefield, B. A. In Anticancer Agents from Natural Products; Cragg, G. M., Kingston, D. G. I., Newman, D. J., Eds.; CRC Press: Boca Raton, FL, 2005: pp 241-265.
28. (d) E7389 website: http:// www.dmgs.com/nda/e7389-080201.html.
29. One of the research focuses has been the development and application of catalytic asymmetric Cr-mediated coupling reactions. Recent results on this subject will be reported in separate papers.
30. For a review on this subject, see: Kolb. H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994. 94, 2483.
31. 2PYR.
32. For a review on substrate-directable chemical reactions, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
33. (a) Jacobsen, E. N.; Marko, I.; Mungall, W. S.: Schroder. G.: Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 1968.
34. (b) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino. G. A.; Härtung. J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.: Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
35. (c) Crispino, G. A.; Jeong, K.-S.; Kolb, H. C.; Wang. Z.-M.; Xu. D.; Sharpless. K. B. J. Org. Chem. 1992. 58, 3785.
36. (d) Becker, H.; Sharpless, K. B. Angew. Chem., Int. Ed. 1996, 35, 448.
37. Garcia-Tellado, F.: Armas. P.; Matrero-Tellado, J. J. Angew. Chem., Int. Ed. 2000. 39, 2727.
38. 4/NMO (22% overall yield from 3).
39. In the new synthesis, the overall yield of 3 →13 was 45%, whereas that of 3 → the intermediate synthetically equivalent to 13 was 13% in the previous synthesis. The over three-time improvement in overall yield is primarily attributed to (1) higher overall yield from 3 to 11. (2) elimination of the benzylation (90%)/debenzylation (75%) steps, and (3) higher efficiency of the hydroxyl-directed reduction (vide infra).
40. 3 in the previous synthesis, whereas both (Z)- and (E)-α,βunsaturated phenylsulfones were smoothly reduced in the new synthesis (vide infra).
41. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983. 48, 4155.
42. Stork, G.; Kahne. D. E. J. Am. Chem. Soc. 1983. 105, 1072.
43. Crabtree, R. H.: Felkin, H.: Fellebeen-Khan, T.: Morris, G. E. J. Organomet. Chem. 1979. 168, 183.
44. In the previous syntheses, we used 14 and 16 as the C27-C35 building block. However, our recent studies demonstrate that 13 is an ideal C27-C35 building block (ref 6).