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There are over 50 known compounds belonging to this class, Perron, F.; Albizati, F. Chem. Rev. 1989, 89, 1617. Westley, J. W.; Seto, H. J. Antibiotics 1979, 32, 959. For other reviews of polyether antibiotics, see Hodgson, K. O. Intra Sci. Chem. Rep. 1974, 8, 27. Westley, J. W. Annu. Rep. Med. Chem. 1975, 10, 246. Pressman, B. C. Annu. Rev. Biochem. 1976, 45, 501.
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2
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There are over 50 known compounds belonging to this class, Perron, F.; Albizati, F. Chem. Rev. 1989, 89, 1617. Westley, J. W.; Seto, H. J. Antibiotics 1979, 32, 959. For other reviews of polyether antibiotics, see Hodgson, K. O. Intra Sci. Chem. Rep. 1974, 8, 27. Westley, J. W. Annu. Rep. Med. Chem. 1975, 10, 246. Pressman, B. C. Annu. Rev. Biochem. 1976, 45, 501.
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0343494311
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There are over 50 known compounds belonging to this class, Perron, F.; Albizati, F. Chem. Rev. 1989, 89, 1617. Westley, J. W.; Seto, H. J. Antibiotics 1979, 32, 959. For other reviews of polyether antibiotics, see Hodgson, K. O. Intra Sci. Chem. Rep. 1974, 8, 27. Westley, J. W. Annu. Rep. Med. Chem. 1975, 10, 246. Pressman, B. C. Annu. Rev. Biochem. 1976, 45, 501.
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There are over 50 known compounds belonging to this class, Perron, F.; Albizati, F. Chem. Rev. 1989, 89, 1617. Westley, J. W.; Seto, H. J. Antibiotics 1979, 32, 959. For other reviews of polyether antibiotics, see Hodgson, K. O. Intra Sci. Chem. Rep. 1974, 8, 27. Westley, J. W. Annu. Rep. Med. Chem. 1975, 10, 246. Pressman, B. C. Annu. Rev. Biochem. 1976, 45, 501.
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Westley, J.W.1
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5
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0017102422
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There are over 50 known compounds belonging to this class, Perron, F.; Albizati, F. Chem. Rev. 1989, 89, 1617. Westley, J. W.; Seto, H. J. Antibiotics 1979, 32, 959. For other reviews of polyether antibiotics, see Hodgson, K. O. Intra Sci. Chem. Rep. 1974, 8, 27. Westley, J. W. Annu. Rep. Med. Chem. 1975, 10, 246. Pressman, B. C. Annu. Rev. Biochem. 1976, 45, 501.
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Mishima, H.1
Junya, I.2
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Ono, M.4
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7
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0343930090
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p Simon, J. Ed., Eiley, New York
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3 synthesis, see Boeckman, R. K.; Jr. Goldman, S. W. The Total Synthesis of Natural Products, p Simon, J. Ed., Eiley, New York, 1988, Vol. 7, pp. 88-92. See also Crimmins, M. T.; Bonkaitis-Davis, D. M.; Hollis, W. G. J. Org. Syn. 1988, 53, 652. For Avermectin synthesis see Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Selnick, H. G.; Hungate, R. J. Am. Chem. Soc. 1989, 111, 2967. Hanessian, S.; Ugolini, A.; Hodges, P. J.; Beaulieu, P.; Dube, A. C. Pure Appl. Chem. 1987, 59, 299.
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Boeckman R.K., Jr.1
Goldman, S.W.2
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8
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0023906983
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3 synthesis, see Boeckman, R. K.; Jr. Goldman, S. W. The Total Synthesis of Natural Products, p Simon, J. Ed., Eiley, New York, 1988, Vol. 7, pp. 88-92. See also Crimmins, M. T.; Bonkaitis-Davis, D. M.; Hollis, W. G. J. Org. Syn. 1988, 53, 652. For Avermectin synthesis see Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Selnick, H. G.; Hungate, R. J. Am. Chem. Soc. 1989, 111, 2967. Hanessian, S.; Ugolini, A.; Hodges, P. J.; Beaulieu, P.; Dube, A. C. Pure Appl. Chem. 1987, 59, 299.
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Bonkaitis-Davis, D.M.2
Hollis, W.G.3
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0024589836
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3 synthesis, see Boeckman, R. K.; Jr. Goldman, S. W. The Total Synthesis of Natural Products, p Simon, J. Ed., Eiley, New York, 1988, Vol. 7, pp. 88-92. See also Crimmins, M. T.; Bonkaitis-Davis, D. M.; Hollis, W. G. J. Org. Syn. 1988, 53, 652. For Avermectin synthesis see Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Selnick, H. G.; Hungate, R. J. Am. Chem. Soc. 1989, 111, 2967. Hanessian, S.; Ugolini, A.; Hodges, P. J.; Beaulieu, P.; Dube, A. C. Pure Appl. Chem. 1987, 59, 299.
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Danishefsky, S.J.1
Armistead, D.M.2
Wincott, F.E.3
Selnick, H.G.4
Hungate, R.5
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10
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84943688112
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3 synthesis, see Boeckman, R. K.; Jr. Goldman, S. W. The Total Synthesis of Natural Products, p Simon, J. Ed., Eiley, New York, 1988, Vol. 7, pp. 88-92. See also Crimmins, M. T.; Bonkaitis-Davis, D. M.; Hollis, W. G. J. Org. Syn. 1988, 53, 652. For Avermectin synthesis see Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Selnick, H. G.; Hungate, R. J. Am. Chem. Soc. 1989, 111, 2967. Hanessian, S.; Ugolini, A.; Hodges, P. J.; Beaulieu, P.; Dube, A. C. Pure Appl. Chem. 1987, 59, 299.
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Hanessian, S.1
Ugolini, A.2
Hodges, P.J.3
Beaulieu, P.4
Dube, A.C.5
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Kurth, M. J.; Brown, E. G.; Hendra, E.; Hope, H. J. Org. Chem. 1985, 50, 1115. Smith, A. B. III; Thompson, A. S. J. Org. Chem. 1984, 49, 1469. Schreiber, S. L.; Sommer, T. J.; Satake, K. Tetrahedron Lett. 1985, 26, 17. Mori, K.; Ikuuaki, M. Tetrahedron 1987, 43, 45.
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Hope, H.4
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0021235938
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Kurth, M. J.; Brown, E. G.; Hendra, E.; Hope, H. J. Org. Chem. 1985, 50, 1115. Smith, A. B. III; Thompson, A. S. J. Org. Chem. 1984, 49, 1469. Schreiber, S. L.; Sommer, T. J.; Satake, K. Tetrahedron Lett. 1985, 26, 17. Mori, K.; Ikuuaki, M. Tetrahedron 1987, 43, 45.
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Smith A.B. III1
Thompson, A.S.2
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Kurth, M. J.; Brown, E. G.; Hendra, E.; Hope, H. J. Org. Chem. 1985, 50, 1115. Smith, A. B. III; Thompson, A. S. J. Org. Chem. 1984, 49, 1469. Schreiber, S. L.; Sommer, T. J.; Satake, K. Tetrahedron Lett. 1985, 26, 17. Mori, K.; Ikuuaki, M. Tetrahedron 1987, 43, 45.
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Schreiber, S.L.1
Sommer, T.J.2
Satake, K.3
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15
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0023138871
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Kurth, M. J.; Brown, E. G.; Hendra, E.; Hope, H. J. Org. Chem. 1985, 50, 1115. Smith, A. B. III; Thompson, A. S. J. Org. Chem. 1984, 49, 1469. Schreiber, S. L.; Sommer, T. J.; Satake, K. Tetrahedron Lett. 1985, 26, 17. Mori, K.; Ikuuaki, M. Tetrahedron 1987, 43, 45.
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Mori, K.1
Ikuuaki, M.2
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0343930089
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Haddad, N.; Abramovich, Z. J. Org. Chem. 1995, 60, 6883. Seebach, D.; Zimmermann, J Helv. Chim. Acta. 1987, 70, 1104. Winkler, J. D.; Hey, J. P.; Hannon, F. J. Heterocycles 1987, 25, 55. Seebach, D.; Noda, Y. Helv. Chim. Acta. 1987, 70, 2137.
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Abramovich, Z.2
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84987486427
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Haddad, N.; Abramovich, Z. J. Org. Chem. 1995, 60, 6883. Seebach, D.; Zimmermann, J Helv. Chim. Acta. 1987, 70, 1104. Winkler, J. D.; Hey, J. P.; Hannon, F. J. Heterocycles 1987, 25, 55. Seebach, D.; Noda, Y. Helv. Chim. Acta. 1987, 70, 2137.
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Seebach, D.1
Zimmermann, J.2
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0006984282
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Haddad, N.; Abramovich, Z. J. Org. Chem. 1995, 60, 6883. Seebach, D.; Zimmermann, J Helv. Chim. Acta. 1987, 70, 1104. Winkler, J. D.; Hey, J. P.; Hannon, F. J. Heterocycles 1987, 25, 55. Seebach, D.; Noda, Y. Helv. Chim. Acta. 1987, 70, 2137.
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Heterocycles
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Winkler, J.D.1
Hey, J.P.2
Hannon, F.J.3
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19
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84928699917
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Haddad, N.; Abramovich, Z. J. Org. Chem. 1995, 60, 6883. Seebach, D.; Zimmermann, J Helv. Chim. Acta. 1987, 70, 1104. Winkler, J. D.; Hey, J. P.; Hannon, F. J. Heterocycles 1987, 25, 55. Seebach, D.; Noda, Y. Helv. Chim. Acta. 1987, 70, 2137.
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Seebach, D.1
Noda, Y.2
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20
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85030202899
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-
note
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All new compounds were characterized by full spectroscopic data, yields refer to chromatographed materials with purity of >95%. Full experimental and spectroscopic data will be published soon.
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22
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85030203315
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note
-
80-W Hanau mercury vapor lamp (Q-81) was used for irradiations via a Pyrex glass filter (λ > 295). All irradiations were carried out in 40-100 mg of benzophenone (triplet sensitizer) in 18 mL acetonitrile as solvent under nitrogen atmosphere. The concentrations always kept below 0.05 M and the reactions were followed by the UV absorption of the starting materials on TLC which usually completed after 45 min at 0°C and 3 h at -70°C.
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-
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23
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0027402610
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The relative stereochemical relationship of the stereogenic centers was determined by NOE-difference. The location of these protons determined by combination of COSY-45, XH-CORR, JMOD-XH methods and was supported by NOE experiments. For determination of similar structures by NMR c.f, Becker, D.; Haddad, N. Tetrahedron 1993, 49, 947. Becker, D.; Haddad, N. Isr. J. Chem. 1989, 29, 303.
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(1993)
Tetrahedron
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, pp. 947
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Becker, D.1
Haddad, N.2
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24
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85005726050
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The relative stereochemical relationship of the stereogenic centers was determined by NOE-difference. The location of these protons determined by combination of COSY-45, XH-CORR, JMOD-XH methods and was supported by NOE experiments. For determination of similar structures by NMR c.f, Becker, D.; Haddad, N. Tetrahedron 1993, 49, 947. Becker, D.; Haddad, N. Isr. J. Chem. 1989, 29, 303.
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Isr. J. Chem.
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Becker, D.1
Haddad, N.2
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26
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0023555158
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For an example of selective Baeyer-Villager oxidation see: Shishido, K.; Takahashi, K.; Fukumoto, K. J. Org. Chem. 1987, 26, 5704. Baldwin, S. W.; Wilkinson, J. M. Tetrahedron Lett. 1979, 20, 2657.
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Shishido, K.1
Takahashi, K.2
Fukumoto, K.3
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27
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0343058378
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For an example of selective Baeyer-Villager oxidation see: Shishido, K.; Takahashi, K.; Fukumoto, K. J. Org. Chem. 1987, 26, 5704. Baldwin, S. W.; Wilkinson, J. M. Tetrahedron Lett. 1979, 20, 2657.
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Baldwin, S.W.1
Wilkinson, J.M.2
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29
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85030205647
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in preparation
-
3) δ 4.20 (q, 4H), 3.90 (dt, J=1.7, 13.2Hz, 1H), 3.72 (dd, J= 8.9, 8.8 Hz, 1H), 3.65 (m, 1H), 3.59 (m, 1H), 3.36 (d, J=16.9 Hz, 1H), 2.93 (dd, J=8.8, 17.0 Hz, 1H), 2.66 (d, J=17.0 Hz, 1H), 2.55 (d, J=14.9 Hz, 1H), 2.41 (dd, J=6.4, 9.9 Hz, 2H), 2.38 (d, J=14.9 Hz, 1H), 1.93 (m, 1H), 1.23 (t, 3H), 1.22 (t, 3H), 1.14 (t, 3H).
-
J. Appl. Cryst.
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Sheldrick, G.M.1
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0022495620
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Winkler, J. D.; Hershberger, P. M.; Spiringer, J. P. Tetrahedron Lett. 1986, 27, 5177.
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Winkler, J.D.1
Hershberger, P.M.2
Spiringer, J.P.3
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31
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37049160091
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Bowers, A.; Halsall, T. G.; Jones, E. R. H.; Lemin, A. J. J. Chem. Soc. 1953, 2548.
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Bowers, A.1
Halsall, T.G.2
Jones, E.R.H.3
Lemin, A.J.4
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32
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85030206457
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note
-
ab=14.7Hz, 1H), 2.19 (d, J=16.9Hz, 1H), 1.82 (dd, J=8.6, 16.7Hz, 1H), 1.43 (bd, J=14.5 Hz, 1H), 1.33 (dd, J=5.7, 8.6Hz, 1H), 1.08 (m, 1H), 0.87 (t, 3H), 0.83 (t, 3H); 20: δ 4.22 (dt, J=6.7, 10.6 Hz,1H), 3.92 (q, 2H), 3.84 (q, 2H), 3.36 (d, J=16.8 Hz, 1H), 3.27 (t, J=11.5 Hz, 1H), 2.91 (q, J=5.2, 11.6Hz, 1H), 2.43 (d, J=16.8 Hz, 1H), 2.31 (d, J=14.6 Hz, 1H), 1.90 (d, J=14.7 Hz, 1H), 1.85 (t, J=7.3 Hz, 1H), 1.74 (t, J=13.2 Hz, 1H), 1.65 (dd, J=8.6, 16.4 Hz, 1H), 1.23 (m, 2H), 0.89 (t, 3H), 0.84 (t, 3H).
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