New Synthetic Route to the C.14-C.38 Segment of Halichondrins

Journal of Organic Chemistry

Volumn 62, Issue 22, 1997, Pages 7552-7553

  Stamos, Dean P ^a   Chen, Sean S ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001635334     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971713b     Document Type: Article

References (28)

1. For the original isolation and structural elucidation of halichondrins, see: (a) Uemura, D.; Takahashi, K.; Yamamoto, T.; Katayama, C.; Tanaka, J.; Okumura, Y.; Hirata, Y. J. Am. Chem. Soc. 1985, 107, 4796-4798. (b) Hirata, Y.; Uemura, D. Pure Appl. Chem. 1986, 58, 701-710.
2. For the original isolation and structural elucidation of halichondrins, see: (a) Uemura, D.; Takahashi, K.; Yamamoto, T.; Katayama, C.; Tanaka, J.; Okumura, Y.; Hirata, Y. J. Am. Chem. Soc. 1985, 107, 4796-4798. (b) Hirata, Y.; Uemura, D. Pure Appl. Chem. 1986, 58, 701-710.
3. For isolation of halichondrin B and homohalichondrin B from Axinella sponge and mechanistic studies of halichondrin cytotoxicity, see: (a) Pettit, G. R.; Herald, C. L.; Boyd, M. R.; Leet, J. E.; Dufresne, C.; Doubek, D. L.; Schmidt, J. M.; Cerny, R. L.; Hooper, J. N. A.; Rutzler, K. C. J. Med. Chem. 1991, 34, 3339-3340. (b) Bai, R.; Paull, K. D.; Herald, C. L.; Pettit, G. R.; Malspeis, L.; Hamel, E. J. Biol. Chem. 1991, 266, 15882-15889.
4. For isolation of halichondrin B and homohalichondrin B from Axinella sponge and mechanistic studies of halichondrin cytotoxicity, see: (a) Pettit, G. R.; Herald, C. L.; Boyd, M. R.; Leet, J. E.; Dufresne, C.; Doubek, D. L.; Schmidt, J. M.; Cerny, R. L.; Hooper, J. N. A.; Rutzler, K. C. J. Med. Chem. 1991, 34, 3339-3340. (b) Bai, R.; Paull, K. D.; Herald, C. L.; Pettit, G. R.; Malspeis, L.; Hamel, E. J. Biol. Chem. 1991, 266, 15882-15889.
5. For isolation and structural elucidation of Isohomohalichondrin from Lissodendoryx sponge, see: Hart, J. B.; Blunt, J. W.; Munro, M. H. G. J. Org. Chem. 1996, 61, 2888-2890 and references therein.
6. For the total synthesis of halichondrin B and norhalichondrin A, see: Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, 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, 3162-3164 and references therein.
7. For more recent synthetic efforts on halichondrins from this laboratory, see: (a) Stamos, D. P.; Taylor, A. G.; Kishi, Y. Tetrahedron Lett. 1996, 37, 8647-8650 and references therein.
8. (b) Stamos, D. P. Harvard Dissertation, Feb, 1997.
9. For synthetic work from other laboratories, see: (a) Cooper, A. J.; Pan, W.; Salomon, R. G. Tetrahedron Lett 1993, 34, 8193-8196 and references therein. (b) Burke, S. D.; Jung, K. W.; Phillips, J. R.; Perri, R. E. Tetrahedron Lett. 1994, 35, 703-706 and references therein. (c) Horita, K.; Hachiya, S.; Ogihara, K.; Yoshida, Y.; Nagasawa, M.; Yonemitsu, O. Heterocycles 1996, 42, 99-104 and references therein.
10. For synthetic work from other laboratories, see: (a) Cooper, A. J.; Pan, W.; Salomon, R. G. Tetrahedron Lett 1993, 34, 8193-8196 and references therein. (b) Burke, S. D.; Jung, K. W.; Phillips, J. R.; Perri, R. E. Tetrahedron Lett. 1994, 35, 703-706 and references therein. (c) Horita, K.; Hachiya, S.; Ogihara, K.; Yoshida, Y.; Nagasawa, M.; Yonemitsu, O. Heterocycles 1996, 42, 99-104 and references therein.
11. For synthetic work from other laboratories, see: (a) Cooper, A. J.; Pan, W.; Salomon, R. G. Tetrahedron Lett 1993, 34, 8193-8196 and references therein. (b) Burke, S. D.; Jung, K. W.; Phillips, J. R.; Perri, R. E. Tetrahedron Lett. 1994, 35, 703-706 and references therein. (c) Horita, K.; Hachiya, S.; Ogihara, K.; Yoshida, Y.; Nagasawa, M.; Yonemitsu, O. Heterocycles 1996, 42, 99-104 and references therein.
12. Minutes, NCI Decision Network Committee, Mar 23, 1992.
13. Kishi, Y.; Fang, F. G.; Forsyth, C. J.; Scola, P. M.; Yoon, S. K. U.S. Patent 5338866, International Patent WO93/17650.
14. 15 to the reaction did not solve this problem.
15. For related subjects, see: Eliel, E. L. Pure Appl. Chem. 1971, 27, 509-525.
16. Kobayashi, N.; Jung, S. H.; Kishi, Y. Unpublished results.
17. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183.
18. E- and Z-unsaturated methyl esters 15 were separated by preparative thin-layer chromatography, and each isomer was separately brought up to 3 to determine the stereoselectivity of the Ni(II)/ Cr(II)-mediated coupling. No difference in the diastereoselectivity was observed between the E- and Z-unsaturated methyl esters. Similarly, the Ni(II)/Cr(II)-mediated coupling of 4 with the vinyl iodides corresponding to 15 but with different ester groups was tested. The observed ratio of the desired and undesired diastereomers at C.27 was >8:1 for the trans-9-hydroxy-10-(1-phenylthio)-9,10-dihydrophenanthrene ester, 6:1 for the trityl ester, and 5:1 for the dibenzosuberyl ester.
19. 4,5 was carried out by converting the TBDPS groups into the corresponding TBS groups.
20. Stamos, D. P.; Sheng, X. C.; Chen, S. S.; Kishi, Y. Tetrahedron Lett. 1997, 38, 6355-6538.
21. Chen, C.; Tagami, K.; Kishi, Y. J. Org. Chem. 1995, 60, 5386-5387.
22. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
23. For the improved preparation of Dess-Martin reagent, see: Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
24. (a) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551-5553.
25. (b) Corey, E. J.; Bakshi, R. K. Tetrahedron Lett. 1990, 31, 611-614.
26. For a review on radical decarboxylation, see: Crich, D. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 7, pp 717-734.
27. 5b With this auxilliary, the diastereoselectivity of the Ni(II)/Cr(II)-mediated coupling was >8:1, but its overall yield from 12 to 3 was lower than the methyl ester series.
28. Barton, D. H. R.; Dowlatshahi, H. A.; Motherwell, W. B.; Villemin, D. J. Chem. Soc., Chem. Commun. 1980, 732-733.