Asymmetric total synthesis of octalactin B using a new and rapid lactonization

Tetrahedron Letters

Volumn 45, Issue 3, 2004, Pages 543-547

  Shiina, Isamu ^a   Oshiumi, Hiromi ^a   Hashizume, Minako ^a   Yamai, Yu Suke ^a   Ibuka, Ryoutarou ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYL 6 NITROBENZOIC ANHYDRIDE; ACETAL DERIVATIVE; ACID ANHYDRIDE; ALDEHYDE DERIVATIVE; AMINOPHENAZONE; BACTERIAL PROTEIN; CYTOTOXIC AGENT; KETENE DERIVATIVE; OCTALACTIN B; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CONTROLLED STUDY; ENANTIOSELECTIVITY; LACTONIZATION; NONHUMAN; OPTICAL ROTATION; SYNTHESIS; TECHNIQUE;

EID: 0346993611     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.213     Document Type: Article

References (51)

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7. (a) Formal syntheses: Buszek K.R., Jeong Y. Tetrahedron Lett. 36:1995;7189-7192 (b) Kodama M., Matsushita M., Terada Y., Takeuchi A., Yoshio S., Fukuyama Y. Chem. Lett. 1997;117-118 (c) Inoue S., Iwabuchi Y., Irie H., Hatakeyama S. Synlett. 1998;735-736 (d) . Partial syntheses: Andrus M.B., Argade A.B. Tetrahedron Lett. 37:1996;5049-5052 (e) Bach J., Garcia J. Tetrahedron Lett. 39:1998;6761-6764 (f) . Other synthetic studies: Bach J., Berenguer R., Garcia J., Vilarrasa J. Tetrahedron Lett. 36:1995;3425-3428 (g) Hulme A.N., Howells G.E. Tetrahedron Lett. 38:1997;8245-8248 (h) Shimoma F., Kusaka H., Wada K., Azami H., Yasunami M., Suzuki T., Hagiwara H., Ando M. J. Org. Chem. 63:1998;920-929 (i) Harrison J.R., Holmes A.B., Collins I. Synlett. 1999;972-974 (j) Anderson E.A., Holmes A.B., Collins I. Tetrahedron Lett. 41:2000;117-121 (k) Bluet G., Campagne J.-M. Synlett. 2000;221-222.
8. (a) Formal syntheses: Buszek K.R., Jeong Y. Tetrahedron Lett. 36:1995;7189-7192 (b) Kodama M., Matsushita M., Terada Y., Takeuchi A., Yoshio S., Fukuyama Y. Chem. Lett. 1997;117-118 (c) Inoue S., Iwabuchi Y., Irie H., Hatakeyama S. Synlett. 1998;735-736 (d) . Partial syntheses: Andrus M.B., Argade A.B. Tetrahedron Lett. 37:1996;5049-5052 (e) Bach J., Garcia J. Tetrahedron Lett. 39:1998;6761-6764 (f) . Other synthetic studies: Bach J., Berenguer R., Garcia J., Vilarrasa J. Tetrahedron Lett. 36:1995;3425-3428 (g) Hulme A.N., Howells G.E. Tetrahedron Lett. 38:1997;8245-8248 (h) Shimoma F., Kusaka H., Wada K., Azami H., Yasunami M., Suzuki T., Hagiwara H., Ando M. J. Org. Chem. 63:1998;920-929 (i) Harrison J.R., Holmes A.B., Collins I. Synlett. 1999;972-974 (j) Anderson E.A., Holmes A.B., Collins I. Tetrahedron Lett. 41:2000;117-121 (k) Bluet G., Campagne J.-M. Synlett. 2000;221-222.
9. (a) Formal syntheses: Buszek K.R., Jeong Y. Tetrahedron Lett. 36:1995;7189-7192 (b) Kodama M., Matsushita M., Terada Y., Takeuchi A., Yoshio S., Fukuyama Y. Chem. Lett. 1997;117-118 (c) Inoue S., Iwabuchi Y., Irie H., Hatakeyama S. Synlett. 1998;735-736 (d) . Partial syntheses: Andrus M.B., Argade A.B. Tetrahedron Lett. 37:1996;5049-5052 (e) Bach J., Garcia J. Tetrahedron Lett. 39:1998;6761-6764 (f) . Other synthetic studies: Bach J., Berenguer R., Garcia J., Vilarrasa J. Tetrahedron Lett. 36:1995;3425-3428 (g) Hulme A.N., Howells G.E. Tetrahedron Lett. 38:1997;8245-8248 (h) Shimoma F., Kusaka H., Wada K., Azami H., Yasunami M., Suzuki T., Hagiwara H., Ando M. J. Org. Chem. 63:1998;920-929 (i) Harrison J.R., Holmes A.B., Collins I. Synlett. 1999;972-974 (j) Anderson E.A., Holmes A.B., Collins I. Tetrahedron Lett. 41:2000;117-121 (k) Bluet G., Campagne J.-M. Synlett. 2000;221-222.
10. (a) Formal syntheses: Buszek K.R., Jeong Y. Tetrahedron Lett. 36:1995;7189-7192 (b) Kodama M., Matsushita M., Terada Y., Takeuchi A., Yoshio S., Fukuyama Y. Chem. Lett. 1997;117-118 (c) Inoue S., Iwabuchi Y., Irie H., Hatakeyama S. Synlett. 1998;735-736 (d) . Partial syntheses: Andrus M.B., Argade A.B. Tetrahedron Lett. 37:1996;5049-5052 (e) Bach J., Garcia J. Tetrahedron Lett. 39:1998;6761-6764 (f) . Other synthetic studies: Bach J., Berenguer R., Garcia J., Vilarrasa J. Tetrahedron Lett. 36:1995;3425-3428 (g) Hulme A.N., Howells G.E. Tetrahedron Lett. 38:1997;8245-8248 (h) Shimoma F., Kusaka H., Wada K., Azami H., Yasunami M., Suzuki T., Hagiwara H., Ando M. J. Org. Chem. 63:1998;920-929 (i) Harrison J.R., Holmes A.B., Collins I. Synlett. 1999;972-974 (j) Anderson E.A., Holmes A.B., Collins I. Tetrahedron Lett. 41:2000;117-121 (k) Bluet G., Campagne J.-M. Synlett. 2000;221-222.
11. (a) Formal syntheses: Buszek K.R., Jeong Y. Tetrahedron Lett. 36:1995;7189-7192 (b) Kodama M., Matsushita M., Terada Y., Takeuchi A., Yoshio S., Fukuyama Y. Chem. Lett. 1997;117-118 (c) Inoue S., Iwabuchi Y., Irie H., Hatakeyama S. Synlett. 1998;735-736 (d) . Partial syntheses: Andrus M.B., Argade A.B. Tetrahedron Lett. 37:1996;5049-5052 (e) Bach J., Garcia J. Tetrahedron Lett. 39:1998;6761-6764 (f) . Other synthetic studies: Bach J., Berenguer R., Garcia J., Vilarrasa J. Tetrahedron Lett. 36:1995;3425-3428 (g) Hulme A.N., Howells G.E. Tetrahedron Lett. 38:1997;8245-8248 (h) Shimoma F., Kusaka H., Wada K., Azami H., Yasunami M., Suzuki T., Hagiwara H., Ando M. J. Org. Chem. 63:1998;920-929 (i) Harrison J.R., Holmes A.B., Collins I. Synlett. 1999;972-974 (j) Anderson E.A., Holmes A.B., Collins I. Tetrahedron Lett. 41:2000;117-121 (k) Bluet G., Campagne J.-M. Synlett. 2000;221-222.
12. (a) Formal syntheses: Buszek K.R., Jeong Y. Tetrahedron Lett. 36:1995;7189-7192 (b) Kodama M., Matsushita M., Terada Y., Takeuchi A., Yoshio S., Fukuyama Y. Chem. Lett. 1997;117-118 (c) Inoue S., Iwabuchi Y., Irie H., Hatakeyama S. Synlett. 1998;735-736 (d) . Partial syntheses: Andrus M.B., Argade A.B. Tetrahedron Lett. 37:1996;5049-5052 (e) Bach J., Garcia J. Tetrahedron Lett. 39:1998;6761-6764 (f) . Other synthetic studies: Bach J., Berenguer R., Garcia J., Vilarrasa J. Tetrahedron Lett. 36:1995;3425-3428 (g) Hulme A.N., Howells G.E. Tetrahedron Lett. 38:1997;8245-8248 (h) Shimoma F., Kusaka H., Wada K., Azami H., Yasunami M., Suzuki T., Hagiwara H., Ando M. J. Org. Chem. 63:1998;920-929 (i) Harrison J.R., Holmes A.B., Collins I. Synlett. 1999;972-974 (j) Anderson E.A., Holmes A.B., Collins I. Tetrahedron Lett. 41:2000;117-121 (k) Bluet G., Campagne J.-M. Synlett. 2000;221-222.
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44. Experimental procedure for the synthesis of the eight-membered ring lactone moiety of octalactins: To a solution of MNBA (6.9 mg, 0.020 mmol) and DMAP (11.3 mg, 0.092 mmol) in toluene (5.3 mL) at room temperature was added 8 (8.7 mg, 0.015 mmol) in toluene (2.4 mL). After the reaction mixture had been stirred for 13 h at room temperature, saturated aqueous sodium hydrogen carbonate was added at 0°C. The mixture was extracted with ethyl acetate and the organic layer was washed with brine, and dried over sodium sulfate. After filtration of the mixture and evaporation of the solvent, the crude product was purified by preparative thin layer chromatography (AcOEt/hexane=1/5) to afford 7 (7.1 mg, 84%) as a colorless oil.
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47. (a) Original S-Py ester methods for the synthesis of macrolactones: Corey E.J., Nicolaou K.C. J. Am. Chem. Soc. 96:1974;5614-5616 (b) Gerlach H., Thalmann A. Helv. Chim. Acta. 57:1974;2661-2663 (c) Corey E.J., Brunelle D.J. Tetrahedron Lett. 17:1976;3409-3412 (d) . See also the synthesis of unsaturated eight-membered ring lactones using S-Py ester method: Nicolaou K.C., McGarry D.G., Somers P.K., Kim B.H., Ogilvie W.W., Yiannikouros G., Prasad C.V.C., Veale C.A., Hark R.R. J. Am. Chem. Soc. 112:1990;6263-6276.
48. (a) Original S-Py ester methods for the synthesis of macrolactones: Corey E.J., Nicolaou K.C. J. Am. Chem. Soc. 96:1974;5614-5616 (b) Gerlach H., Thalmann A. Helv. Chim. Acta. 57:1974;2661-2663 (c) Corey E.J., Brunelle D.J. Tetrahedron Lett. 17:1976;3409-3412 (d) . See also the synthesis of unsaturated eight-membered ring lactones using S-Py ester method: Nicolaou K.C., McGarry D.G., Somers P.K., Kim B.H., Ogilvie W.W., Yiannikouros G., Prasad C.V.C., Veale C.A., Hark R.R. J. Am. Chem. Soc. 112:1990;6263-6276.
49. (a) Original S-Py ester methods for the synthesis of macrolactones: Corey E.J., Nicolaou K.C. J. Am. Chem. Soc. 96:1974;5614-5616 (b) Gerlach H., Thalmann A. Helv. Chim. Acta. 57:1974;2661-2663 (c) Corey E.J., Brunelle D.J. Tetrahedron Lett. 17:1976;3409-3412 (d) . See also the synthesis of unsaturated eight-membered ring lactones using S-Py ester method: Nicolaou K.C., McGarry D.G., Somers P.K., Kim B.H., Ogilvie W.W., Yiannikouros G., Prasad C.V.C., Veale C.A., Hark R.R. J. Am. Chem. Soc. 112:1990;6263-6276.
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51. [2b].