Synthetic studies on halichondrins: A practical synthesis of the C.1-C.13 segment

Tetrahedron Letters

Volumn 37, Issue 48, 1996, Pages 8643-8646

  Stamos, Dean P ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HALICHONDRIN B; MACROLIDE; POLYETHER ANTIBIOTIC AGENT;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0030602154     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)01999-5     Document Type: Article

References (21)

1. 1. (a) Uemura, D.; Takahashi, K.; Yamamoto, T.; Katayama, C.; Tanaka,J.; Okumura, Y.; Hirata, Y. J. Am. Chem. Soc. 1985, 107, 4796-4798.
2. (b) Hirata, Y.; Uemura, D. Pure Appl. Chem. 1986, 58, 701-710.
3. (c) Bai, R.; Paull, K. D.; Herald, C. L.; Pettit, G. R.; Malspeis, L.;Hamel, E. J. Biol. Chem. 1991, 266, 15882-15889.
4. (d) Halichondrin B and homohalichondrin B were also isolated from Acinella sponge: 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. Isohomohalichondrin has been isolated from Lissodendoryx sponge: see Hart, J. B.; Blunt, J. W.; Munro, H. G. J. Org. Chem., 1996, 61, 2888-2890 and references cited therein.
5. (d) Halichondrin B and homohalichondrin B were also isolated from Acinella sponge: 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. Isohomohalichondrin has been isolated from Lissodendoryx sponge: see Hart, J. B.; Blunt, J. W.; Munro, H. G. J. Org. Chem., 1996, 61, 2888-2890 and references cited therein.
6. 2. For synthetic work from this laboratory, see: Duan, J. J.-W.; Kishi, Y. Tetrahedron Lett. 1993, 34, 7541-7544 and references cited therein. For the stereoselectivity of the Ni(II)/Cr(II)-mediated coupling, see footnote 10 of this reference.
7. 3. For synthetic work from other labs, see: (a) Cooper, A. J.; Pan, A.; Salomon, R. G. Tetrahedron Lett. 1993, 34, 8193-8196 and references cited therein.
8. (b) Burke, S. D.; Jung, K. W.; Phillips, J. R.; Perri, R. E. Tetrahedron Lett. 1994, 35, 703-706 and references cited therein.
9. (c) Horita, K.; Sakurai, Y.; Nagasawa, M.; Maeno, K.; Hachiya, S.; Yonemitsu, O. Synlett 1994, 46-48 and references cited therein.
10. 4. Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc., 1986,108, 7408-7410.
11. 3PCHCOMe/PhMe/reflux; 60% yield). However, this reaction was not only very slow, but proceeded with epimerization of the C.3 stereocenter (2.5:1 mixture).
12. 6. The diacetate acetonide 4 with R=benzyl, adamantoyl, TBDPS, and 9-anthracenylmethyl was prepared from D-ribono-γ-lactone in good overall yields. The details of this synthesis will be given elsewhere; Dean P. Stamos, Harvard Dissertation, 1996.
13. II. The degree of stereoselectivity depends on the degree of the steric interaction between the C.10 substitutent and the incoming nucleophile; see Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978. (formula presented)
14. 8. Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3943-3946.
15. 9. For an excellent review on double stereodifferentiation, see Masamune, S; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Eng., 1985, 24, 1-76.
16. 10. Lohray, B. B.; Kalantar, T. H.; Kim, B. M.; Park, C. Y.; Shibata, T.; Wai, J. S. M.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 2041-2044. For a review on catalytic asymmetric dihydroxylation, see Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev., 1994, 94, 2483-2547.
17. 10. Lohray, B. B.; Kalantar, T. H.; Kim, B. M.; Park, C. Y.; Shibata, T.; Wai, J. S. M.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 2041-2044. For a review on catalytic asymmetric dihydroxylation, see Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev., 1994, 94, 2483-2547.
18. 3 with equal efficiency (b.p. 51-53 °C , 0.1 mmHg).
19. 12. Earlier work in this group (see reference 2) indicated that the initial oxy-Michael adduct was a 1:1 mixture at C.3. This ratio could be easily raised to 1:0 favoring the desired product upon extended treatment with TRITON-B(OMe).
20. 2 in 90% yield (b.p. 90-92 °C, 30 mmHg). For the preparation of the above vinylstannane, see: Colvin, E. W. Silicon Reagents in Organic Synthesis, 1988, p 10, Academic Press.
21. 14. Stamos, D. P.; Taylor, A. G.; Kishi, Y. the accompanying letter.