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1
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0000651888
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For part 1, see: Bures, E.; Spinazze, P. G.; Beese, G.; Hunt, I. R.; Rogers, C.; Keay, B. A. J. Org. Chem. 1997, 62, 8741.
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(1997)
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Bures, E.1
Spinazze, P.G.2
Beese, G.3
Hunt, I.R.4
Rogers, C.5
Keay, B.A.6
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11
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0001176061
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For some recent examples, see: (a) Keay, B. A.; Dibble, P. W. Compr. Heterocycl. Chem. II 1996, 2, 395. (b) Fraga, B. M. Nat. Prod. Rep. 1992, 5, 217. (c) Faulkner, D. J. Nat. Prod. Rep. 1992, 9, 323. (d) Fraga, B. M. Nat. Prod. Rep. 1992, 9, 557. (e) Fraga, B. M. Nat. Prod. Rep. 1991, 8, 61. (f) Faulkner, D. J. Nat. Prod. Rep. 1991, 8, 269. (g) Fraga, B. M. Nat. Prod. Rep. 1990, 7, 515. (h) Faulkner, D. J. Nat. Prod. Rep. 1988, 5, 269. (i) Hanson, J. R. Nat. Prod. Rep. 1989, 5, 347. For the use of 3,4-disubstituted furans as intermediates in synthesis, see: (j) Froborg, J.; Magnusson, G.; Thoren, S. J. Org. Chem. 1975, 40, 1595. (k) Lipshutz, B. H. Chem. Rev. 1986, 86, 795. (l) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. Chem. Lett. 1987, 2257. (m) Jung, M. E.; Usui, Y.; Vu, C. T. Tetrahedron Lett. 1987, 28, 5977. (n) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. J. Org. Chem. 1988, 53, 5464. (o) Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Lett. 1991, 32, 4761. (p) Eberbach, W.; Laber, N.; Bussenius, J.; Fritz, H.; Rihs, G. Chem. Ber. 1993, 126, 975.
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(1996)
Compr. Heterocycl. Chem. II
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Keay, B.A.1
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12
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0026881596
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For some recent examples, see: (a) Keay, B. A.; Dibble, P. W. Compr. Heterocycl. Chem. II 1996, 2, 395. (b) Fraga, B. M. Nat. Prod. Rep. 1992, 5, 217. (c) Faulkner, D. J. Nat. Prod. Rep. 1992, 9, 323. (d) Fraga, B. M. Nat. Prod. Rep. 1992, 9, 557. (e) Fraga, B. M. Nat. Prod. Rep. 1991, 8, 61. (f) Faulkner, D. J. Nat. Prod. Rep. 1991, 8, 269. (g) Fraga, B. M. Nat. Prod. Rep. 1990, 7, 515. (h) Faulkner, D. J. Nat. Prod. Rep. 1988, 5, 269. (i) Hanson, J. R. Nat. Prod. Rep. 1989, 5, 347. For the use of 3,4-disubstituted furans as intermediates in synthesis, see: (j) Froborg, J.; Magnusson, G.; Thoren, S. J. Org. Chem. 1975, 40, 1595. (k) Lipshutz, B. H. Chem. Rev. 1986, 86, 795. (l) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. Chem. Lett. 1987, 2257. (m) Jung, M. E.; Usui, Y.; Vu, C. T. Tetrahedron Lett. 1987, 28, 5977. (n) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. J. Org. Chem. 1988, 53, 5464. (o) Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Lett. 1991, 32, 4761. (p) Eberbach, W.; Laber, N.; Bussenius, J.; Fritz, H.; Rihs, G. Chem. Ber. 1993, 126, 975.
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(1992)
Nat. Prod. Rep.
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Fraga, B.M.1
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13
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0000372491
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For some recent examples, see: (a) Keay, B. A.; Dibble, P. W. Compr. Heterocycl. Chem. II 1996, 2, 395. (b) Fraga, B. M. Nat. Prod. Rep. 1992, 5, 217. (c) Faulkner, D. J. Nat. Prod. Rep. 1992, 9, 323. (d) Fraga, B. M. Nat. Prod. Rep. 1992, 9, 557. (e) Fraga, B. M. Nat. Prod. Rep. 1991, 8, 61. (f) Faulkner, D. J. Nat. Prod. Rep. 1991, 8, 269. (g) Fraga, B. M. Nat. Prod. Rep. 1990, 7, 515. (h) Faulkner, D. J. Nat. Prod. Rep. 1988, 5, 269. (i) Hanson, J. R. Nat. Prod. Rep. 1989, 5, 347. For the use of 3,4-disubstituted furans as intermediates in synthesis, see: (j) Froborg, J.; Magnusson, G.; Thoren, S. J. Org. Chem. 1975, 40, 1595. (k) Lipshutz, B. H. Chem. Rev. 1986, 86, 795. (l) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. Chem. Lett. 1987, 2257. (m) Jung, M. E.; Usui, Y.; Vu, C. T. Tetrahedron Lett. 1987, 28, 5977. (n) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. J. Org. Chem. 1988, 53, 5464. (o) Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Lett. 1991, 32, 4761. (p) Eberbach, W.; Laber, N.; Bussenius, J.; Fritz, H.; Rihs, G. Chem. Ber. 1993, 126, 975.
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(1992)
Nat. Prod. Rep.
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Faulkner, D.J.1
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14
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0013603594
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For some recent examples, see: (a) Keay, B. A.; Dibble, P. W. Compr. Heterocycl. Chem. II 1996, 2, 395. (b) Fraga, B. M. Nat. Prod. Rep. 1992, 5, 217. (c) Faulkner, D. J. Nat. Prod. Rep. 1992, 9, 323. (d) Fraga, B. M. Nat. Prod. Rep. 1992, 9, 557. (e) Fraga, B. M. Nat. Prod. Rep. 1991, 8, 61. (f) Faulkner, D. J. Nat. Prod. Rep. 1991, 8, 269. (g) Fraga, B. M. Nat. Prod. Rep. 1990, 7, 515. (h) Faulkner, D. J. Nat. Prod. Rep. 1988, 5, 269. (i) Hanson, J. R. Nat. Prod. Rep. 1989, 5, 347. For the use of 3,4-disubstituted furans as intermediates in synthesis, see: (j) Froborg, J.; Magnusson, G.; Thoren, S. J. Org. Chem. 1975, 40, 1595. (k) Lipshutz, B. H. Chem. Rev. 1986, 86, 795. (l) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. Chem. Lett. 1987, 2257. (m) Jung, M. E.; Usui, Y.; Vu, C. T. Tetrahedron Lett. 1987, 28, 5977. (n) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. J. Org. Chem. 1988, 53, 5464. (o) Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Lett. 1991, 32, 4761. (p) Eberbach, W.; Laber, N.; Bussenius, J.; Fritz, H.; Rihs, G. Chem. Ber. 1993, 126, 975.
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(1992)
Nat. Prod. Rep.
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Fraga, B.M.1
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15
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1542582561
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For some recent examples, see: (a) Keay, B. A.; Dibble, P. W. Compr. Heterocycl. Chem. II 1996, 2, 395. (b) Fraga, B. M. Nat. Prod. Rep. 1992, 5, 217. (c) Faulkner, D. J. Nat. Prod. Rep. 1992, 9, 323. (d) Fraga, B. M. Nat. Prod. Rep. 1992, 9, 557. (e) Fraga, B. M. Nat. Prod. Rep. 1991, 8, 61. (f) Faulkner, D. J. Nat. Prod. Rep. 1991, 8, 269. (g) Fraga, B. M. Nat. Prod. Rep. 1990, 7, 515. (h) Faulkner, D. J. Nat. Prod. Rep. 1988, 5, 269. (i) Hanson, J. R. Nat. Prod. Rep. 1989, 5, 347. For the use of 3,4-disubstituted furans as intermediates in synthesis, see: (j) Froborg, J.; Magnusson, G.; Thoren, S. J. Org. Chem. 1975, 40, 1595. (k) Lipshutz, B. H. Chem. Rev. 1986, 86, 795. (l) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. Chem. Lett. 1987, 2257. (m) Jung, M. E.; Usui, Y.; Vu, C. T. Tetrahedron Lett. 1987, 28, 5977. (n) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. J. Org. Chem. 1988, 53, 5464. (o) Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Lett. 1991, 32, 4761. (p) Eberbach, W.; Laber, N.; Bussenius, J.; Fritz, H.; Rihs, G. Chem. Ber. 1993, 126, 975.
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(1991)
Nat. Prod. Rep.
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Fraga, B.M.1
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16
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1542477941
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For some recent examples, see: (a) Keay, B. A.; Dibble, P. W. Compr. Heterocycl. Chem. II 1996, 2, 395. (b) Fraga, B. M. Nat. Prod. Rep. 1992, 5, 217. (c) Faulkner, D. J. Nat. Prod. Rep. 1992, 9, 323. (d) Fraga, B. M. Nat. Prod. Rep. 1992, 9, 557. (e) Fraga, B. M. Nat. Prod. Rep. 1991, 8, 61. (f) Faulkner, D. J. Nat. Prod. Rep. 1991, 8, 269. (g) Fraga, B. M. Nat. Prod. Rep. 1990, 7, 515. (h) Faulkner, D. J. Nat. Prod. Rep. 1988, 5, 269. (i) Hanson, J. R. Nat. Prod. Rep. 1989, 5, 347. For the use of 3,4-disubstituted furans as intermediates in synthesis, see: (j) Froborg, J.; Magnusson, G.; Thoren, S. J. Org. Chem. 1975, 40, 1595. (k) Lipshutz, B. H. Chem. Rev. 1986, 86, 795. (l) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. Chem. Lett. 1987, 2257. (m) Jung, M. E.; Usui, Y.; Vu, C. T. Tetrahedron Lett. 1987, 28, 5977. (n) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. J. Org. Chem. 1988, 53, 5464. (o) Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Lett. 1991, 32, 4761. (p) Eberbach, W.; Laber, N.; Bussenius, J.; Fritz, H.; Rihs, G. Chem. Ber. 1993, 126, 975.
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(1991)
Nat. Prod. Rep.
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Faulkner, D.J.1
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0343608470
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For some recent examples, see: (a) Keay, B. A.; Dibble, P. W. Compr. Heterocycl. Chem. II 1996, 2, 395. (b) Fraga, B. M. Nat. Prod. Rep. 1992, 5, 217. (c) Faulkner, D. J. Nat. Prod. Rep. 1992, 9, 323. (d) Fraga, B. M. Nat. Prod. Rep. 1992, 9, 557. (e) Fraga, B. M. Nat. Prod. Rep. 1991, 8, 61. (f) Faulkner, D. J. Nat. Prod. Rep. 1991, 8, 269. (g) Fraga, B. M. Nat. Prod. Rep. 1990, 7, 515. (h) Faulkner, D. J. Nat. Prod. Rep. 1988, 5, 269. (i) Hanson, J. R. Nat. Prod. Rep. 1989, 5, 347. For the use of 3,4-disubstituted furans as intermediates in synthesis, see: (j) Froborg, J.; Magnusson, G.; Thoren, S. J. Org. Chem. 1975, 40, 1595. (k) Lipshutz, B. H. Chem. Rev. 1986, 86, 795. (l) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. Chem. Lett. 1987, 2257. (m) Jung, M. E.; Usui, Y.; Vu, C. T. Tetrahedron Lett. 1987, 28, 5977. (n) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. J. Org. Chem. 1988, 53, 5464. (o) Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Lett. 1991, 32, 4761. (p) Eberbach, W.; Laber, N.; Bussenius, J.; Fritz, H.; Rihs, G. Chem. Ber. 1993, 126, 975.
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(1990)
Nat. Prod. Rep.
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For some recent examples, see: (a) Keay, B. A.; Dibble, P. W. Compr. Heterocycl. Chem. II 1996, 2, 395. (b) Fraga, B. M. Nat. Prod. Rep. 1992, 5, 217. (c) Faulkner, D. J. Nat. Prod. Rep. 1992, 9, 323. (d) Fraga, B. M. Nat. Prod. Rep. 1992, 9, 557. (e) Fraga, B. M. Nat. Prod. Rep. 1991, 8, 61. (f) Faulkner, D. J. Nat. Prod. Rep. 1991, 8, 269. (g) Fraga, B. M. Nat. Prod. Rep. 1990, 7, 515. (h) Faulkner, D. J. Nat. Prod. Rep. 1988, 5, 269. (i) Hanson, J. R. Nat. Prod. Rep. 1989, 5, 347. For the use of 3,4-disubstituted furans as intermediates in synthesis, see: (j) Froborg, J.; Magnusson, G.; Thoren, S. J. Org. Chem. 1975, 40, 1595. (k) Lipshutz, B. H. Chem. Rev. 1986, 86, 795. (l) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. Chem. Lett. 1987, 2257. (m) Jung, M. E.; Usui, Y.; Vu, C. T. Tetrahedron Lett. 1987, 28, 5977. (n) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. J. Org. Chem. 1988, 53, 5464. (o) Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Lett. 1991, 32, 4761. (p) Eberbach, W.; Laber, N.; Bussenius, J.; Fritz, H.; Rihs, G. Chem. Ber. 1993, 126, 975.
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Nat. Prod. Rep.
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For some recent examples, see: (a) Keay, B. A.; Dibble, P. W. Compr. Heterocycl. Chem. II 1996, 2, 395. (b) Fraga, B. M. Nat. Prod. Rep. 1992, 5, 217. (c) Faulkner, D. J. Nat. Prod. Rep. 1992, 9, 323. (d) Fraga, B. M. Nat. Prod. Rep. 1992, 9, 557. (e) Fraga, B. M. Nat. Prod. Rep. 1991, 8, 61. (f) Faulkner, D. J. Nat. Prod. Rep. 1991, 8, 269. (g) Fraga, B. M. Nat. Prod. Rep. 1990, 7, 515. (h) Faulkner, D. J. Nat. Prod. Rep. 1988, 5, 269. (i) Hanson, J. R. Nat. Prod. Rep. 1989, 5, 347. For the use of 3,4-disubstituted furans as intermediates in synthesis, see: (j) Froborg, J.; Magnusson, G.; Thoren, S. J. Org. Chem. 1975, 40, 1595. (k) Lipshutz, B. H. Chem. Rev. 1986, 86, 795. (l) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. Chem. Lett. 1987, 2257. (m) Jung, M. E.; Usui, Y.; Vu, C. T. Tetrahedron Lett. 1987, 28, 5977. (n) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. J. Org. Chem. 1988, 53, 5464. (o) Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Lett. 1991, 32, 4761. (p) Eberbach, W.; Laber, N.; Bussenius, J.; Fritz, H.; Rihs, G. Chem. Ber. 1993, 126, 975.
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Nat. Prod. Rep.
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For some recent examples, see: (a) Keay, B. A.; Dibble, P. W. Compr. Heterocycl. Chem. II 1996, 2, 395. (b) Fraga, B. M. Nat. Prod. Rep. 1992, 5, 217. (c) Faulkner, D. J. Nat. Prod. Rep. 1992, 9, 323. (d) Fraga, B. M. Nat. Prod. Rep. 1992, 9, 557. (e) Fraga, B. M. Nat. Prod. Rep. 1991, 8, 61. (f) Faulkner, D. J. Nat. Prod. Rep. 1991, 8, 269. (g) Fraga, B. M. Nat. Prod. Rep. 1990, 7, 515. (h) Faulkner, D. J. Nat. Prod. Rep. 1988, 5, 269. (i) Hanson, J. R. Nat. Prod. Rep. 1989, 5, 347. For the use of 3,4-disubstituted furans as intermediates in synthesis, see: (j) Froborg, J.; Magnusson, G.; Thoren, S. J. Org. Chem. 1975, 40, 1595. (k) Lipshutz, B. H. Chem. Rev. 1986, 86, 795. (l) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. Chem. Lett. 1987, 2257. (m) Jung, M. E.; Usui, Y.; Vu, C. T. Tetrahedron Lett. 1987, 28, 5977. (n) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. J. Org. Chem. 1988, 53, 5464. (o) Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Lett. 1991, 32, 4761. (p) Eberbach, W.; Laber, N.; Bussenius, J.; Fritz, H.; Rihs, G. Chem. Ber. 1993, 126, 975.
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For some recent examples, see: (a) Keay, B. A.; Dibble, P. W. Compr. Heterocycl. Chem. II 1996, 2, 395. (b) Fraga, B. M. Nat. Prod. Rep. 1992, 5, 217. (c) Faulkner, D. J. Nat. Prod. Rep. 1992, 9, 323. (d) Fraga, B. M. Nat. Prod. Rep. 1992, 9, 557. (e) Fraga, B. M. Nat. Prod. Rep. 1991, 8, 61. (f) Faulkner, D. J. Nat. Prod. Rep. 1991, 8, 269. (g) Fraga, B. M. Nat. Prod. Rep. 1990, 7, 515. (h) Faulkner, D. J. Nat. Prod. Rep. 1988, 5, 269. (i) Hanson, J. R. Nat. Prod. Rep. 1989, 5, 347. For the use of 3,4-disubstituted furans as intermediates in synthesis, see: (j) Froborg, J.; Magnusson, G.; Thoren, S. J. Org. Chem. 1975, 40, 1595. (k) Lipshutz, B. H. Chem. Rev. 1986, 86, 795. (l) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. Chem. Lett. 1987, 2257. (m) Jung, M. E.; Usui, Y.; Vu, C. T. Tetrahedron Lett. 1987, 28, 5977. (n) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. J. Org. Chem. 1988, 53, 5464. (o) Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Lett. 1991, 32, 4761. (p) Eberbach, W.; Laber, N.; Bussenius, J.; Fritz, H.; Rihs, G. Chem. Ber. 1993, 126, 975.
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For some recent examples, see: (a) Keay, B. A.; Dibble, P. W. Compr. Heterocycl. Chem. II 1996, 2, 395. (b) Fraga, B. M. Nat. Prod. Rep. 1992, 5, 217. (c) Faulkner, D. J. Nat. Prod. Rep. 1992, 9, 323. (d) Fraga, B. M. Nat. Prod. Rep. 1992, 9, 557. (e) Fraga, B. M. Nat. Prod. Rep. 1991, 8, 61. (f) Faulkner, D. J. Nat. Prod. Rep. 1991, 8, 269. (g) Fraga, B. M. Nat. Prod. Rep. 1990, 7, 515. (h) Faulkner, D. J. Nat. Prod. Rep. 1988, 5, 269. (i) Hanson, J. R. Nat. Prod. Rep. 1989, 5, 347. For the use of 3,4-disubstituted furans as intermediates in synthesis, see: (j) Froborg, J.; Magnusson, G.; Thoren, S. J. Org. Chem. 1975, 40, 1595. (k) Lipshutz, B. H. Chem. Rev. 1986, 86, 795. (l) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. Chem. Lett. 1987, 2257. (m) Jung, M. E.; Usui, Y.; Vu, C. T. Tetrahedron Lett. 1987, 28, 5977. (n) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. J. Org. Chem. 1988, 53, 5464. (o) Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Lett. 1991, 32, 4761. (p) Eberbach, W.; Laber, N.; Bussenius, J.; Fritz, H.; Rihs, G. Chem. Ber. 1993, 126, 975.
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For some recent examples, see: (a) Keay, B. A.; Dibble, P. W. Compr. Heterocycl. Chem. II 1996, 2, 395. (b) Fraga, B. M. Nat. Prod. Rep. 1992, 5, 217. (c) Faulkner, D. J. Nat. Prod. Rep. 1992, 9, 323. (d) Fraga, B. M. Nat. Prod. Rep. 1992, 9, 557. (e) Fraga, B. M. Nat. Prod. Rep. 1991, 8, 61. (f) Faulkner, D. J. Nat. Prod. Rep. 1991, 8, 269. (g) Fraga, B. M. Nat. Prod. Rep. 1990, 7, 515. (h) Faulkner, D. J. Nat. Prod. Rep. 1988, 5, 269. (i) Hanson, J. R. Nat. Prod. Rep. 1989, 5, 347. For the use of 3,4-disubstituted furans as intermediates in synthesis, see: (j) Froborg, J.; Magnusson, G.; Thoren, S. J. Org. Chem. 1975, 40, 1595. (k) Lipshutz, B. H. Chem. Rev. 1986, 86, 795. (l) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. Chem. Lett. 1987, 2257. (m) Jung, M. E.; Usui, Y.; Vu, C. T. Tetrahedron Lett. 1987, 28, 5977. (n) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. J. Org. Chem. 1988, 53, 5464. (o) Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Lett. 1991, 32, 4761. (p) Eberbach, W.; Laber, N.; Bussenius, J.; Fritz, H.; Rihs, G. Chem. Ber. 1993, 126, 975.
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For some recent examples, see: (a) Keay, B. A.; Dibble, P. W. Compr. Heterocycl. Chem. II 1996, 2, 395. (b) Fraga, B. M. Nat. Prod. Rep. 1992, 5, 217. (c) Faulkner, D. J. Nat. Prod. Rep. 1992, 9, 323. (d) Fraga, B. M. Nat. Prod. Rep. 1992, 9, 557. (e) Fraga, B. M. Nat. Prod. Rep. 1991, 8, 61. (f) Faulkner, D. J. Nat. Prod. Rep. 1991, 8, 269. (g) Fraga, B. M. Nat. Prod. Rep. 1990, 7, 515. (h) Faulkner, D. J. Nat. Prod. Rep. 1988, 5, 269. (i) Hanson, J. R. Nat. Prod. Rep. 1989, 5, 347. For the use of 3,4-disubstituted furans as intermediates in synthesis, see: (j) Froborg, J.; Magnusson, G.; Thoren, S. J. Org. Chem. 1975, 40, 1595. (k) Lipshutz, B. H. Chem. Rev. 1986, 86, 795. (l) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. Chem. Lett. 1987, 2257. (m) Jung, M. E.; Usui, Y.; Vu, C. T. Tetrahedron Lett. 1987, 28, 5977. (n) Katagiri, N.; Akatsuka, H.; Haneda, T.; Kaneko, C. J. Org. Chem. 1988, 53, 5464. (o) Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Lett. 1991, 32, 4761. (p) Eberbach, W.; Laber, N.; Bussenius, J.; Fritz, H.; Rihs, G. Chem. Ber. 1993, 126, 975.
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1H NMR spectra, we normally use a pulse delay of 60 s.
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An alternative explanation is that the acidity of the C-4 hydrogen atom has increased relative to that of the C-5 hydrogen atom due to electronic factors resulting from the presence of a silicon atom at C-2 of the furan ring. Semiempirical calculations (PM3) on 2-(trimethylsilyl)-3-(hydroxymethyl)furan indicated that the electronic density at the furan carbon atoms and the C-4 and C-5 hydrogen atoms were not significantly changed relative to the electronic densities calculated for similar atoms in 3-(hydroxymethyl)furan; therefore we believe stereoelectronic factors are not the driving force for the observed C-4 lithiation.
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4 dihedral angle ranging from +36° to +85°.
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We do not understand why compound 3 lithiates exclusively at C-4 in DME in the absence of an additive. The bidendate nature of this solvent may not be the reason since the lithiation of 3 in a THF-TMEDA mixture resulted in a C-4:C-5 mixture.
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