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For recent reviews: (a) Zafra-Polo, M. C.; Figadère, B.; Gallardo, T.; Tormo, J. R.; Cortes, D. Phytochemistry 1998, 48, 1087. (b) Alali, F. Q.; Liu, X. X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504.
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Phytochemistry
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For recent reviews: (a) Zafra-Polo, M. C.; Figadère, B.; Gallardo, T.; Tormo, J. R.; Cortes, D. Phytochemistry 1998, 48, 1087. (b) Alali, F. Q.; Liu, X. X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504.
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For reviews of acetogenin synthesis see ref. 1 and: (a) Hoppe, R.; Scharf, H. D. Synthesis 1995, 1447. (b) Figadère, B.; Cavé, A. In Studies in Natural Products Chemistry, Vol. 18; Rahman, A. U., Ed.; Elsevier Science: Amsterdam, 1996, 193-227. (c) Marshall, J. A.; Hinkle, K. W.; Hagedorn, C. E. Isr. J. Chem. 1997, 37, 97. (d) Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G.; Appendino, G. Chemtracts 1998, 11, 803.
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For reviews of acetogenin synthesis see ref. 1 and: (a) Hoppe, R.; Scharf, H. D. Synthesis 1995, 1447. (b) Figadère, B.; Cavé, A. In Studies in Natural Products Chemistry, Vol. 18; Rahman, A. U., Ed.; Elsevier Science: Amsterdam, 1996, 193-227. (c) Marshall, J. A.; Hinkle, K. W.; Hagedorn, C. E. Isr. J. Chem. 1997, 37, 97. (d) Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G.; Appendino, G. Chemtracts 1998, 11, 803.
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For reviews of acetogenin synthesis see ref. 1 and: (a) Hoppe, R.; Scharf, H. D. Synthesis 1995, 1447. (b) Figadère, B.; Cavé, A. In Studies in Natural Products Chemistry, Vol. 18; Rahman, A. U., Ed.; Elsevier Science: Amsterdam, 1996, 193-227. (c) Marshall, J. A.; Hinkle, K. W.; Hagedorn, C. E. Isr. J. Chem. 1997, 37, 97. (d) Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G.; Appendino, G. Chemtracts 1998, 11, 803.
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For reviews of acetogenin synthesis see ref. 1 and: (a) Hoppe, R.; Scharf, H. D. Synthesis 1995, 1447. (b) Figadère, B.; Cavé, A. In Studies in Natural Products Chemistry, Vol. 18; Rahman, A. U., Ed.; Elsevier Science: Amsterdam, 1996, 193-227. (c) Marshall, J. A.; Hinkle, K. W.; Hagedorn, C. E. Isr. J. Chem. 1997, 37, 97. (d) Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G.; Appendino, G. Chemtracts 1998, 11, 803.
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Zanardi, F.2
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Appendino, G.5
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0033519292
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For selected recent approaches to the synthesis of acetogenins: (a) Baurle, S.; Hoppen, S.; Koert, U. Angew. Chem. Int. Ed. 1999, 38, 1263. (b) Marshall, J. A.; Piettre, A.; Paige, M. A.; Valeriote, F. J. Org. Chem. 2003, 68, 1771. (c) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 4017. (d) Trost, B. M.; Calkins, T. L.; Bochet, C. G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2632. (e) Hanessian, S.; Grillo, T. A. J. Org. Chem. 1998, 63, 1049. (f) Kuriyama, W.; Ishigami, K.; Kitahara, T. Heterocycles 1999, 50, 981. (g) Yu, Q.; Wu, Y. K.; Ding, H.; Wu, Y. L. J. Chem. Soc., Perkin Trans. 1 1999, 1183. (h) Ruan, Z. M.; Dabideen, D.; Blumenstein, M.; Mootoo, D. R. Tetrahedron 2000, 56, 9203. (i) Zanardi, F.; Battistini, L.; Rassu, G.; Auzzas, L.; Pinna, L.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 2048. (j) Hu, T. S.; Yu, Q.; Wu, Y. L.; Wu, Y. K. J. Org. Chem. 2001, 66, 853. (k) Dixon, D. J.; Ley, S. V.; Reynolds, D. J. Chem.-Eur. J. 2002, 8, 1621. (l) Cecil, A. R. L.; Brown, R. C. D. Org. Lett. 2002, 4, 3715.
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Baurle, S.1
Hoppen, S.2
Koert, U.3
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0037424528
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For selected recent approaches to the synthesis of acetogenins: (a) Baurle, S.; Hoppen, S.; Koert, U. Angew. Chem. Int. Ed. 1999, 38, 1263. (b) Marshall, J. A.; Piettre, A.; Paige, M. A.; Valeriote, F. J. Org. Chem. 2003, 68, 1771. (c) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 4017. (d) Trost, B. M.; Calkins, T. L.; Bochet, C. G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2632. (e) Hanessian, S.; Grillo, T. A. J. Org. Chem. 1998, 63, 1049. (f) Kuriyama, W.; Ishigami, K.; Kitahara, T. Heterocycles 1999, 50, 981. (g) Yu, Q.; Wu, Y. K.; Ding, H.; Wu, Y. L. J. Chem. Soc., Perkin Trans. 1 1999, 1183. (h) Ruan, Z. M.; Dabideen, D.; Blumenstein, M.; Mootoo, D. R. Tetrahedron 2000, 56, 9203. (i) Zanardi, F.; Battistini, L.; Rassu, G.; Auzzas, L.; Pinna, L.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 2048. (j) Hu, T. S.; Yu, Q.; Wu, Y. L.; Wu, Y. K. J. Org. Chem. 2001, 66, 853. (k) Dixon, D. J.; Ley, S. V.; Reynolds, D. J. Chem.-Eur. J. 2002, 8, 1621. (l) Cecil, A. R. L.; Brown, R. C. D. Org. Lett. 2002, 4, 3715.
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J. Org. Chem.
, vol.68
, pp. 1771
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Marshall, J.A.1
Piettre, A.2
Paige, M.A.3
Valeriote, F.4
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9
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0032577030
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For selected recent approaches to the synthesis of acetogenins: (a) Baurle, S.; Hoppen, S.; Koert, U. Angew. Chem. Int. Ed. 1999, 38, 1263. (b) Marshall, J. A.; Piettre, A.; Paige, M. A.; Valeriote, F. J. Org. Chem. 2003, 68, 1771. (c) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 4017. (d) Trost, B. M.; Calkins, T. L.; Bochet, C. G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2632. (e) Hanessian, S.; Grillo, T. A. J. Org. Chem. 1998, 63, 1049. (f) Kuriyama, W.; Ishigami, K.; Kitahara, T. Heterocycles 1999, 50, 981. (g) Yu, Q.; Wu, Y. K.; Ding, H.; Wu, Y. L. J. Chem. Soc., Perkin Trans. 1 1999, 1183. (h) Ruan, Z. M.; Dabideen, D.; Blumenstein, M.; Mootoo, D. R. Tetrahedron 2000, 56, 9203. (i) Zanardi, F.; Battistini, L.; Rassu, G.; Auzzas, L.; Pinna, L.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 2048. (j) Hu, T. S.; Yu, Q.; Wu, Y. L.; Wu, Y. K. J. Org. Chem. 2001, 66, 853. (k) Dixon, D. J.; Ley, S. V.; Reynolds, D. J. Chem.-Eur. J. 2002, 8, 1621. (l) Cecil, A. R. L.; Brown, R. C. D. Org. Lett. 2002, 4, 3715.
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J. Am. Chem. Soc.
, vol.120
, pp. 4017
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Sinha, S.C.1
Sinha, A.2
Sinha, S.C.3
Keinan, E.4
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10
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0031573966
-
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For selected recent approaches to the synthesis of acetogenins: (a) Baurle, S.; Hoppen, S.; Koert, U. Angew. Chem. Int. Ed. 1999, 38, 1263. (b) Marshall, J. A.; Piettre, A.; Paige, M. A.; Valeriote, F. J. Org. Chem. 2003, 68, 1771. (c) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 4017. (d) Trost, B. M.; Calkins, T. L.; Bochet, C. G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2632. (e) Hanessian, S.; Grillo, T. A. J. Org. Chem. 1998, 63, 1049. (f) Kuriyama, W.; Ishigami, K.; Kitahara, T. Heterocycles 1999, 50, 981. (g) Yu, Q.; Wu, Y. K.; Ding, H.; Wu, Y. L. J. Chem. Soc., Perkin Trans. 1 1999, 1183. (h) Ruan, Z. M.; Dabideen, D.; Blumenstein, M.; Mootoo, D. R. Tetrahedron 2000, 56, 9203. (i) Zanardi, F.; Battistini, L.; Rassu, G.; Auzzas, L.; Pinna, L.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 2048. (j) Hu, T. S.; Yu, Q.; Wu, Y. L.; Wu, Y. K. J. Org. Chem. 2001, 66, 853. (k) Dixon, D. J.; Ley, S. V.; Reynolds, D. J. Chem.-Eur. J. 2002, 8, 1621. (l) Cecil, A. R. L.; Brown, R. C. D. Org. Lett. 2002, 4, 3715.
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Angew. Chem., Int. Ed. Engl.
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Trost, B.M.1
Calkins, T.L.2
Bochet, C.G.3
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11
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0032548960
-
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For selected recent approaches to the synthesis of acetogenins: (a) Baurle, S.; Hoppen, S.; Koert, U. Angew. Chem. Int. Ed. 1999, 38, 1263. (b) Marshall, J. A.; Piettre, A.; Paige, M. A.; Valeriote, F. J. Org. Chem. 2003, 68, 1771. (c) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 4017. (d) Trost, B. M.; Calkins, T. L.; Bochet, C. G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2632. (e) Hanessian, S.; Grillo, T. A. J. Org. Chem. 1998, 63, 1049. (f) Kuriyama, W.; Ishigami, K.; Kitahara, T. Heterocycles 1999, 50, 981. (g) Yu, Q.; Wu, Y. K.; Ding, H.; Wu, Y. L. J. Chem. Soc., Perkin Trans. 1 1999, 1183. (h) Ruan, Z. M.; Dabideen, D.; Blumenstein, M.; Mootoo, D. R. Tetrahedron 2000, 56, 9203. (i) Zanardi, F.; Battistini, L.; Rassu, G.; Auzzas, L.; Pinna, L.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 2048. (j) Hu, T. S.; Yu, Q.; Wu, Y. L.; Wu, Y. K. J. Org. Chem. 2001, 66, 853. (k) Dixon, D. J.; Ley, S. V.; Reynolds, D. J. Chem.-Eur. J. 2002, 8, 1621. (l) Cecil, A. R. L.; Brown, R. C. D. Org. Lett. 2002, 4, 3715.
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J. Org. Chem.
, vol.63
, pp. 1049
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Hanessian, S.1
Grillo, T.A.2
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12
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0033117367
-
-
For selected recent approaches to the synthesis of acetogenins: (a) Baurle, S.; Hoppen, S.; Koert, U. Angew. Chem. Int. Ed. 1999, 38, 1263. (b) Marshall, J. A.; Piettre, A.; Paige, M. A.; Valeriote, F. J. Org. Chem. 2003, 68, 1771. (c) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 4017. (d) Trost, B. M.; Calkins, T. L.; Bochet, C. G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2632. (e) Hanessian, S.; Grillo, T. A. J. Org. Chem. 1998, 63, 1049. (f) Kuriyama, W.; Ishigami, K.; Kitahara, T. Heterocycles 1999, 50, 981. (g) Yu, Q.; Wu, Y. K.; Ding, H.; Wu, Y. L. J. Chem. Soc., Perkin Trans. 1 1999, 1183. (h) Ruan, Z. M.; Dabideen, D.; Blumenstein, M.; Mootoo, D. R. Tetrahedron 2000, 56, 9203. (i) Zanardi, F.; Battistini, L.; Rassu, G.; Auzzas, L.; Pinna, L.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 2048. (j) Hu, T. S.; Yu, Q.; Wu, Y. L.; Wu, Y. K. J. Org. Chem. 2001, 66, 853. (k) Dixon, D. J.; Ley, S. V.; Reynolds, D. J. Chem.-Eur. J. 2002, 8, 1621. (l) Cecil, A. R. L.; Brown, R. C. D. Org. Lett. 2002, 4, 3715.
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(1999)
Heterocycles
, vol.50
, pp. 981
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Kuriyama, W.1
Ishigami, K.2
Kitahara, T.3
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13
-
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0001491461
-
-
For selected recent approaches to the synthesis of acetogenins: (a) Baurle, S.; Hoppen, S.; Koert, U. Angew. Chem. Int. Ed. 1999, 38, 1263. (b) Marshall, J. A.; Piettre, A.; Paige, M. A.; Valeriote, F. J. Org. Chem. 2003, 68, 1771. (c) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 4017. (d) Trost, B. M.; Calkins, T. L.; Bochet, C. G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2632. (e) Hanessian, S.; Grillo, T. A. J. Org. Chem. 1998, 63, 1049. (f) Kuriyama, W.; Ishigami, K.; Kitahara, T. Heterocycles 1999, 50, 981. (g) Yu, Q.; Wu, Y. K.; Ding, H.; Wu, Y. L. J. Chem. Soc., Perkin Trans. 1 1999, 1183. (h) Ruan, Z. M.; Dabideen, D.; Blumenstein, M.; Mootoo, D. R. Tetrahedron 2000, 56, 9203. (i) Zanardi, F.; Battistini, L.; Rassu, G.; Auzzas, L.; Pinna, L.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 2048. (j) Hu, T. S.; Yu, Q.; Wu, Y. L.; Wu, Y. K. J. Org. Chem. 2001, 66, 853. (k) Dixon, D. J.; Ley, S. V.; Reynolds, D. J. Chem.-Eur. J. 2002, 8, 1621. (l) Cecil, A. R. L.; Brown, R. C. D. Org. Lett. 2002, 4, 3715.
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(1999)
J. Chem. Soc., Perkin Trans. 1
, pp. 1183
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Yu, Q.1
Wu, Y.K.2
Ding, H.3
Wu, Y.L.4
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14
-
-
0034680726
-
-
For selected recent approaches to the synthesis of acetogenins: (a) Baurle, S.; Hoppen, S.; Koert, U. Angew. Chem. Int. Ed. 1999, 38, 1263. (b) Marshall, J. A.; Piettre, A.; Paige, M. A.; Valeriote, F. J. Org. Chem. 2003, 68, 1771. (c) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 4017. (d) Trost, B. M.; Calkins, T. L.; Bochet, C. G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2632. (e) Hanessian, S.; Grillo, T. A. J. Org. Chem. 1998, 63, 1049. (f) Kuriyama, W.; Ishigami, K.; Kitahara, T. Heterocycles 1999, 50, 981. (g) Yu, Q.; Wu, Y. K.; Ding, H.; Wu, Y. L. J. Chem. Soc., Perkin Trans. 1 1999, 1183. (h) Ruan, Z. M.; Dabideen, D.; Blumenstein, M.; Mootoo, D. R. Tetrahedron 2000, 56, 9203. (i) Zanardi, F.; Battistini, L.; Rassu, G.; Auzzas, L.; Pinna, L.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 2048. (j) Hu, T. S.; Yu, Q.; Wu, Y. L.; Wu, Y. K. J. Org. Chem. 2001, 66, 853. (k) Dixon, D. J.; Ley, S. V.; Reynolds, D. J. Chem.-Eur. J. 2002, 8, 1621. (l) Cecil, A. R. L.; Brown, R. C. D. Org. Lett. 2002, 4, 3715.
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(2000)
Tetrahedron
, vol.56
, pp. 9203
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Ruan, Z.M.1
Dabideen, D.2
Blumenstein, M.3
Mootoo, D.R.4
-
15
-
-
0034616281
-
-
For selected recent approaches to the synthesis of acetogenins: (a) Baurle, S.; Hoppen, S.; Koert, U. Angew. Chem. Int. Ed. 1999, 38, 1263. (b) Marshall, J. A.; Piettre, A.; Paige, M. A.; Valeriote, F. J. Org. Chem. 2003, 68, 1771. (c) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 4017. (d) Trost, B. M.; Calkins, T. L.; Bochet, C. G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2632. (e) Hanessian, S.; Grillo, T. A. J. Org. Chem. 1998, 63, 1049. (f) Kuriyama, W.; Ishigami, K.; Kitahara, T. Heterocycles 1999, 50, 981. (g) Yu, Q.; Wu, Y. K.; Ding, H.; Wu, Y. L. J. Chem. Soc., Perkin Trans. 1 1999, 1183. (h) Ruan, Z. M.; Dabideen, D.; Blumenstein, M.; Mootoo, D. R. Tetrahedron 2000, 56, 9203. (i) Zanardi, F.; Battistini, L.; Rassu, G.; Auzzas, L.; Pinna, L.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 2048. (j) Hu, T. S.; Yu, Q.; Wu, Y. L.; Wu, Y. K. J. Org. Chem. 2001, 66, 853. (k) Dixon, D. J.; Ley, S. V.; Reynolds, D. J. Chem.-Eur. J. 2002, 8, 1621. (l) Cecil, A. R. L.; Brown, R. C. D. Org. Lett. 2002, 4, 3715.
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J. Org. Chem.
, vol.65
, pp. 2048
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Zanardi, F.1
Battistini, L.2
Rassu, G.3
Auzzas, L.4
Pinna, L.5
Marzocchi, L.6
Acquotti, D.7
Casiraghi, G.8
-
16
-
-
0035830542
-
-
For selected recent approaches to the synthesis of acetogenins: (a) Baurle, S.; Hoppen, S.; Koert, U. Angew. Chem. Int. Ed. 1999, 38, 1263. (b) Marshall, J. A.; Piettre, A.; Paige, M. A.; Valeriote, F. J. Org. Chem. 2003, 68, 1771. (c) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 4017. (d) Trost, B. M.; Calkins, T. L.; Bochet, C. G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2632. (e) Hanessian, S.; Grillo, T. A. J. Org. Chem. 1998, 63, 1049. (f) Kuriyama, W.; Ishigami, K.; Kitahara, T. Heterocycles 1999, 50, 981. (g) Yu, Q.; Wu, Y. K.; Ding, H.; Wu, Y. L. J. Chem. Soc., Perkin Trans. 1 1999, 1183. (h) Ruan, Z. M.; Dabideen, D.; Blumenstein, M.; Mootoo, D. R. Tetrahedron 2000, 56, 9203. (i) Zanardi, F.; Battistini, L.; Rassu, G.; Auzzas, L.; Pinna, L.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 2048. (j) Hu, T. S.; Yu, Q.; Wu, Y. L.; Wu, Y. K. J. Org. Chem. 2001, 66, 853. (k) Dixon, D. J.; Ley, S. V.; Reynolds, D. J. Chem.-Eur. J. 2002, 8, 1621. (l) Cecil, A. R. L.; Brown, R. C. D. Org. Lett. 2002, 4, 3715.
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J. Org. Chem.
, vol.66
, pp. 853
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Hu, T.S.1
Yu, Q.2
Wu, Y.L.3
Wu, Y.K.4
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17
-
-
0037006821
-
-
For selected recent approaches to the synthesis of acetogenins: (a) Baurle, S.; Hoppen, S.; Koert, U. Angew. Chem. Int. Ed. 1999, 38, 1263. (b) Marshall, J. A.; Piettre, A.; Paige, M. A.; Valeriote, F. J. Org. Chem. 2003, 68, 1771. (c) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 4017. (d) Trost, B. M.; Calkins, T. L.; Bochet, C. G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2632. (e) Hanessian, S.; Grillo, T. A. J. Org. Chem. 1998, 63, 1049. (f) Kuriyama, W.; Ishigami, K.; Kitahara, T. Heterocycles 1999, 50, 981. (g) Yu, Q.; Wu, Y. K.; Ding, H.; Wu, Y. L. J. Chem. Soc., Perkin Trans. 1 1999, 1183. (h) Ruan, Z. M.; Dabideen, D.; Blumenstein, M.; Mootoo, D. R. Tetrahedron 2000, 56, 9203. (i) Zanardi, F.; Battistini, L.; Rassu, G.; Auzzas, L.; Pinna, L.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 2048. (j) Hu, T. S.; Yu, Q.; Wu, Y. L.; Wu, Y. K. J. Org. Chem. 2001, 66, 853. (k) Dixon, D. J.; Ley, S. V.; Reynolds, D. J. Chem.-Eur. J. 2002, 8, 1621. (l) Cecil, A. R. L.; Brown, R. C. D. Org. Lett. 2002, 4, 3715.
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Chem.-Eur. J.
, vol.8
, pp. 1621
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Dixon, D.J.1
Ley, S.V.2
Reynolds, D.J.3
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18
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0037126217
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A single diastereoisomer 3 was isolated from the reaction mixture, although oxidative cyclisation of similar substrates has been found to proceed with a diastereoselectivity of approximately 6:1.
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