Formal total synthesis of altohyrtin C (spongistatin 2). Part 1: Aldol approach to unite AB and CD spiroacetals

Tetrahedron Letters

Volumn 44, Issue 42, 2003, Pages 7741-7745

  Terauchi, Takeshi ^a   Terauchi, Taro ^a   Sato, Ippei ^a   Shoji, Wataru ^a   Tsukada, Tomoharu ^a   Tsunoda, Takashi ^a   Kanoh, Naoki ^a,b   Nakata, Masaya ^a  

^a KEIO UNIVERSITY   (Japan)

^b Japan Science and Technology Agency   (Japan)

Author keywords

Aldol reaction; Altohyrtins; Spongistatins; Stereoselective synthesis

Indexed keywords

ACETAL DERIVATIVE; ANTINEOPLASTIC AGENT; SPIRO COMPOUND; SPONGISTATIN 2;

ALDOL REACTION; ARTICLE; CHIRALITY; DESS MARTIN OXIDATION; DRUG SYNTHESIS; EPIMERIZATION; MUKAIYAMA REACTION; NUCLEAR OVERHAUSER EFFECT; SILYLATION; STEREOCHEMISTRY;

EID: 0141746177     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.08.082     Document Type: Article

References (53)

1. Kobayashi M., Aoki S., Sakai H., Kawazoe K., Kihara N., Sasaki T., Kitagawa I. Tetrahedron Lett. 34:1993;2795-2798.
2. Pettit G.R., Cichacz Z.A., Gao F., Herald C.L., Boyd M.R., Schmidt J.M., Hooper J.N.A. J. Org. Chem. 58:1993;1302-1304.
3. Fusetani N., Shinoda K., Matsunaga S. J. Am. Chem. Soc. 115:1993;3977-3981.
4. Evans D.A., Coleman P.J., Dias L.C. Angew. Chem., Int. Ed. Engl. 36:1997;2738-2741.
5. Evans D.A., Trotter B.W., Côté B., Coleman P.J. Angew. Chem., Int. Ed. Engl. 36:1997;2741-2744.
6. Evans D.A., Trotter B.W., Côté B., Coleman P.J., Dias L.C., Tyler A.N. Angew. Chem., Int. Ed. Engl. 36:1997;2744-2747.
7. Evans D.A., Trotter B.W., Coleman P.J., Côté B., Dias L.C., Rajapakse H.A., Tyler A.N. Tetrahedron. 55:1999;8671-8726.
8. Guo J., Duffy K.J., Stevens K.L., Dalko P.I., Roth R.M., Hayward M.M., Kishi Y. Angew. Chem., Int. Ed. 37:1998;187-192.
9. Hayward M.M., Roth R.M., Duffy K.J., Dalko P.I., Stevens K.L., Guo J., Kishi Y. Angew. Chem., Int. Ed. 37:1998;192-196.
10. Smith A.B. III, Doughty V.A., Lin Q., Zhuang L., McBriar M.D., Boldi A.M., Moser W.H., Murase N., Nakayama K., Sobukawa M. Angew. Chem., Int. Ed. 40:2001;191-195.
11. Smith A.B. III, Lin Q., Doughty V.A., Zhuang L., McBriar M.D., Kerns J.K., Brook C.S., Murase N., Nakayama K. Angew. Chem., Int. Ed. 40:2001;196-199.
12. Smith A.B. III, Zhu W., Shirakami S., Sfouggatakis C., Doughty V.A., Bennett C.S., Sakamoto Y. Org. Lett. 5:2003;761-764. and references cited therein.
13. Paterson I., Chen D.Y.-K., Coster M.J., Acena J.L., Bach J., Gibson K.R., Keown L.E., Oballa R.M., Trieselmann T., Wallace D.J., Hodgson A.P., Norcross R.D. Angew. Chem., Int. Ed. 40:2001;4055-4060. and references cited therein.
14. Crimmins M.T., Katz J.D., Washburn D.G., Allwein S.P., McAtee L.F. J. Am. Chem. Soc. 124:2002;5661-5663. and references cited therein.
15. Cho I.H., Paquette L.A. Heterocycles. 58:2002;43-46. and references cited therein.
16. Zuev D., Paquette L.A. Org. Lett. 2:2000;679-682.
17. Holson E.B., Roush W.R. Org. Lett. 4:2002;3719-3722. and references cited therein.
18. Wallace G.A., Scott R.W., Heathcock C.H. J. Org. Chem. 65:2000;4145-4152. and references cited therein.
19. Lemaire-Audoire S., Vogel P. J. Org. Chem. 65:2000;3346-3356. and references cited therein.
20. Samadi M., Munoz-Letelier C., Poigny S., Guyot M. Tetrahedron Lett. 41:2000;3349-3353.
21. Uckun F.M., Mao C., Vassilev A.O., Huang H., Jan S.-T. Bioorg. Med. Chem. Lett. 10:2000;541-545.
22. Anderson J.C., MaDermott B.P., Griffin E.J. Tetrahedron. 56:2000;8747-8767. and references cited therein.
23. Barrett A.G.M., Braddock D.C., de Koning P.D., White A.J.P., Williams D.J. J. Org. Chem. 65:2000;375-380.
24. Dunkel R., Treu J., Hoffmann H.M.R. Tetrahedron: Asymmetry. 10:1999;1539-1549.
25. Kary P.D., Roberts S.M., Watson D.J. Tetrahedron: Asymmetry. 10:1999;213-216. and references cited therein.
26. Fernandez-Megia E., Gourlaouen N., Ley S.V., Rowlands G.J. Synlett. 1998;991-994.
27. Zemribo R., Mead K.T. Tetrahedron Lett. 39:1998;3891-3894. and references cited therein.
28. Terauchi T., Nakata M. Tetrahedron Lett. 39:1998;3795-3798.
29. Terauchi T., Terauchi T., Sato I., Tsukada T., Kanoh N., Nakata M. Tetrahedron Lett. 41:2000;2649-2653.
30. Terauchi T., Morita M., Kimijima K., Nakamura Y., Hayashi G., Tanaka T., Kanoh N., Nakata M. Tetrahedron Lett. 42:2001;5505-5508.
31. The C23 stereocenter is reported to be epimerized to the natural congener in the final stage of the synthesis. See Ref. 4b.
32. Dess D.B., Martin J.C. J. Org. Chem. 48:1983;4155-4156.
33. Dess D.B., Martin J.C. J. Am. Chem. Soc. 113:1991;7277-7287.
34. Mukaiyama T., Banno K., Narasaka K. J. Am. Chem. Soc. 96:1974;7503-7509.
35. Evans D.A., Dart M.J., Duffy J.L., Yang M.G. J. Am. Chem. Soc. 118:1996;4322-4343.
36. 2-hexane, -40°C; (g) Dess-Martin oxidation.
37. 2-hexane, -40°C; (g) Dess-Martin oxidation.
38. 2-hexane, -40°C; (g) Dess-Martin oxidation.
39. 2-hexane, -40°C; (g) Dess-Martin oxidation.
40. 2-hexane, -40°C; (g) Dess-Martin oxidation.
41. 2-hexane, -40°C; (g) Dess-Martin oxidation.
42. 2-hexane, -40°C; (g) Dess-Martin oxidation.
43. 2-hexane, -40°C; (g) Dess-Martin oxidation.
44. Kiyooka S., Kuroda H., Shimasaki Y. Tetrahedron Lett. 27:1986;3009-3012.
45. Rychnovsky S.D., Skalitzky D.J. Tetrahedron Lett. 31:1990;945-948.
46. Rychnovsky S.D., Rogers B.N., Yang G. J. Org. Chem. 58:1993;3511-3515.
47. Rychnovsky S.D., Yang G., Powers J.P. J. Org. Chem. 58:1993;5251-5255.
48. Rychnovsky S.D., Rogers B.N., Richardson T.I. Acc. Chem. Res. 31:1998;9-17.
49. Ohtani I., Kusumi T., Kashman Y., Kakisawa H. J. Am. Chem. Soc. 113:1991;4092-4096.
50. Since it was difficult to determine the stereochemistry at the newly formed carbon centers (C14, C15), it was tentatively assigned as depicted, depending on the model studies as described above. Moreover, the fact that the coupling constants (J=8.8, 2.4 Hz) around the C15 stereocenter of acetate 24 (R=Ac) were close to those (J=9.2, 2.8 Hz) of the Paquette's compound supports the assignment. See Ref. 7b.
51. Other groups also experienced a similar epimerization in their synthetic studies. See Refs. 3a and 4a.
52. Paquette et al. reported that they succeeded in the methylenation of the C13 ketone with Tebbe reagent albeit in low yield. See Ref. 7b.
53. Terauchi T., Tanaka T., Terauchi T., Morita M., Kimijima K., Sato I., Shoji W., Nakamura Y., Tsukada T., Tsunoda T., Hayashi G., Kanoh N., Nakata M. Tetrahedron Lett. 44:2003;7747-7751.