-
2
-
-
0001834676
-
Tetrahedron symposia-in-print number 58: Fluoroorganic chemistry: Synthetic challenges and biomedicinal rewards
-
(b) Tetrahedron Symposia-in-print Number 58: Fluoroorganic Chemistry: Synthetic Challenges and Biomedicinal Rewards Tetrahedron 1996, 52, 1-330.
-
(1996)
Tetrahedron
, vol.52
, pp. 1-330
-
-
-
3
-
-
0014665768
-
-
2. Fluorination in medicinal chemistry, see e.g. (a) Goldman, P. Science 1969, 164, 1123-1130.
-
(1969)
Science
, vol.164
, pp. 1123-1130
-
-
Goldman, P.1
-
5
-
-
0023237559
-
-
(c) Welch, J. T. Tetrahedron 1987, 43, 3123-3197.
-
(1987)
Tetrahedron
, vol.43
, pp. 3123-3197
-
-
Welch, J.T.1
-
7
-
-
0003490832
-
-
Elsevier Science Publishers B.V., Amsterdam
-
(e) Studies in Organic Chemistry 48: Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications (Filler, R.; Kobayashi, Y.; Yagupolskii, L. M., Eds), Elsevier Science Publishers B.V., Amsterdam, 1993.
-
(1993)
Studies in Organic Chemistry 48: Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications
-
-
Filler, R.1
Kobayashi, Y.2
Yagupolskii, L.M.3
-
8
-
-
0000788606
-
-
Weinstein, B. (Ed). Marcel Dekker Inc., New York
-
3. For reviews on amide bond isosteres, see (a) Spatola, A. in Chemistry and Biochemistry of Amino Acids, Peptides and Proteins. Vol. 7. Weinstein, B. (Ed). Marcel Dekker Inc., New York, 1983, pp 267-357.
-
(1983)
Chemistry and Biochemistry of Amino Acids, Peptides and Proteins
, vol.7
, pp. 267-357
-
-
Spatola, A.1
-
12
-
-
84989585190
-
-
and references therein
-
4. For syntheses of (E)-alkene dipeptide isosteres, see (a) Ibuka, T. J. Synth. Org. Chem. Jpn. 1992, 50, 953-962 and references therein.
-
(1992)
J. Synth. Org. Chem. Jpn.
, vol.50
, pp. 953-962
-
-
Ibuka, T.1
-
13
-
-
0001219079
-
-
and references therein
-
(b) Ibuka, T., Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 999-1015 and references therein.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 999-1015
-
-
Ibuka, T.1
Mimura, N.2
Aoyama, H.3
Akaji, M.4
Ohno, H.5
Miwa, Y.6
Taga, T.7
Nakai, K.8
Tamamura, H.9
Fujii, N.10
Yamamoto, Y.11
-
14
-
-
0022649952
-
-
5. For syntheses and use of the fluorovinyl moiety as an amide bond isostere, see: a) Abraham, R. J.; Ellison, S. L. R.; Schonholzer, P.; Thomas, W. A. Tetrahedron 1986, 42, 2101-2110.
-
(1986)
Tetrahedron
, vol.42
, pp. 2101-2110
-
-
Abraham, R.J.1
Ellison, S.L.R.2
Schonholzer, P.3
Thomas, W.A.4
-
15
-
-
0025695128
-
-
(b) Allmendinger, T.; Furet, P.; Hungerbühler, E. Tetrahedron Lett. 1990, 31, 7297-7300.
-
(1990)
Tetrahedron Lett.
, vol.31
, pp. 7297-7300
-
-
Allmendinger, T.1
Furet, P.2
Hungerbühler, E.3
-
16
-
-
0025663110
-
-
(c) Allmendinger, T.; Felder, E.; Hungerbühler, E. Tetrahedron Lett. 1990, 31, 7301-7304.
-
(1990)
Tetrahedron Lett.
, vol.31
, pp. 7301-7304
-
-
Allmendinger, T.1
Felder, E.2
Hungerbühler, E.3
-
17
-
-
0027968473
-
-
(d) Boros, L. G.; De Corte, B. Gimi, R. H.; Welch, J. T.; Wu, Y.; Handschumacher, R. E. Tetrahedron Lett. 1994, 35, 6033-6036.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 6033-6036
-
-
Boros, L.G.1
De Corte, B.2
Gimi, R.H.3
Welch, J.T.4
Wu, Y.5
Handschumacher, R.E.6
-
19
-
-
0029656172
-
-
(f) Takeuchi, Y.; Yamada, A.; Suzuki, T.; Koizumi, T. Tetrahedron 1996, 52, 225-232.
-
(1996)
Tetrahedron
, vol.52
, pp. 225-232
-
-
Takeuchi, Y.1
Yamada, A.2
Suzuki, T.3
Koizumi, T.4
-
24
-
-
0027432004
-
-
(c) Resnati, G. Tetrahedron 1993, 49, 9385-9445.
-
(1993)
Tetrahedron
, vol.49
, pp. 9385-9445
-
-
Resnati, G.1
-
26
-
-
0000420715
-
-
8. For a review on diethylaminosulfur trifluoride (DAST) and its reactions, see Hudlický, M. Org. React. 1988, 35, 513-637.
-
(1988)
Org. React.
, vol.35
, pp. 513-637
-
-
Hudlický, M.1
-
27
-
-
33847800447
-
-
9. DAST has been used in fluorinations of alcohols, see e.g. (a) Middleton, W. J. J. Org. Chem. 1975, 40, 574-578.
-
(1975)
J. Org. Chem.
, vol.40
, pp. 574-578
-
-
Middleton, W.J.1
-
30
-
-
0003082963
-
-
(d) Rosenbrook, Jr., W.; Riley, D. A.; Lartey, P. A. Tetrahedron Lett. 1985, 26, 3-4.
-
(1985)
Tetrahedron Lett.
, vol.26
, pp. 3-4
-
-
Rosenbrook W., Jr.1
Riley, D.A.2
Lartey, P.A.3
-
33
-
-
37049080574
-
-
(g) Yamauchi, T.; Hattori, K.; Ikeda, S.; Tamaki; K. J. Chem. Soc., Perkin Trans. 1 1990, 1683-1685.
-
(1990)
J. Chem. Soc., Perkin Trans. 1
, pp. 1683-1685
-
-
Yamauchi, T.1
Hattori, K.2
Ikeda, S.3
Tamaki, K.4
-
34
-
-
0027249848
-
-
(h) Canfarini, F.; Giolitti, A.; Guidi, A.; Pasqui, F.; Pestellini, V.; Arcamone, F. Tetrahedron Lett. 1993, 34, 4697-4700.
-
(1993)
Tetrahedron Lett.
, vol.34
, pp. 4697-4700
-
-
Canfarini, F.1
Giolitti, A.2
Guidi, A.3
Pasqui, F.4
Pestellini, V.5
Arcamone, F.6
-
36
-
-
0032485422
-
-
(j) Demange, L.; Ménez, A.; Dugave, C. Tetrahedron Lett. 1998, 39, 1169-1172.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 1169-1172
-
-
Demange, L.1
Ménez, A.2
Dugave, C.3
-
37
-
-
0029895833
-
-
10. For a review of difluorination reactions, see Tozer, M. J.; Herpin, T. F. Tetrahedron 1996, 52, 619-8683.
-
(1996)
Tetrahedron
, vol.52
, pp. 8619-8683
-
-
Tozer, M.J.1
Herpin, T.F.2
-
39
-
-
0009541401
-
-
(b) Sharma, R. A.; Kavai, I.; Fu, Y. L.; Bobek, M. Tetrahedron Lett. 1977, 3433-3436.
-
(1977)
Tetrahedron Lett.
, pp. 3433-3436
-
-
Sharma, R.A.1
Kavai, I.2
Fu, Y.L.3
Bobek, M.4
-
40
-
-
0002607513
-
-
(c) Bird, T. G. C.; Fredericks, P. M.; Jones, E. R. H.; Meakins, G. D. J. Chem. Soc., Chem. Commun. 1979, 65-66.
-
(1979)
J. Chem. Soc., Chem. Commun.
, pp. 65-66
-
-
Bird, T.G.C.1
Fredericks, P.M.2
Jones, E.R.H.3
Meakins, G.D.4
-
43
-
-
0001276191
-
-
(f) El-Laghdach, A.; Echarri, R.; Matheu, M. I.; Barrena, M. I.; Castillón, S.; García, J. J. Org. Chem. 1991, 56, 4556-4559.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 4556-4559
-
-
El-Laghdach, A.1
Echarri, R.2
Matheu, M.I.3
Barrena, M.I.4
Castillón, S.5
García, J.6
-
44
-
-
33751392349
-
-
(g) Sun, W.-C.; Ng, C.-S.; Prestwich, G. D. J. Org. Chem. 1992, 57, 132-137.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 132-137
-
-
Sun, W.-C.1
Ng, C.-S.2
Prestwich, G.D.3
-
45
-
-
0029125171
-
-
(h) Parisi, M. F.; Gattuso, G.; Notti, A.; Raymo, F. M.; Abeles, R. H. J. Org. Chem. 1995, 60, 5174-5179.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 5174-5179
-
-
Parisi, M.F.1
Gattuso, G.2
Notti, A.3
Raymo, F.M.4
Abeles, R.H.5
-
46
-
-
0032473803
-
-
(i) Fernández, R.; Matheu, M. I.; Echarri, R.; Castillón, S. Tetrahedron 1998, 54, 3523-3532.
-
(1998)
Tetrahedron
, vol.54
, pp. 3523-3532
-
-
Fernández, R.1
Matheu, M.I.2
Echarri, R.3
Castillón, S.4
-
47
-
-
0028242889
-
-
11. Kim, B. M.; Guare, J. P.; Hanifin, C. M.; Arford-Bickerstaff, D. J.; Vacca, J. P.; Ball, R. G. Tetrahedron Lett. 1994, 35, 5153-5156.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 5153-5156
-
-
Kim, B.M.1
Guare, J.P.2
Hanifin, C.M.3
Arford-Bickerstaff, D.J.4
Vacca, J.P.5
Ball, R.G.6
-
48
-
-
0009488155
-
-
12. With time this conjugated double bond could also be epoxidized. A conjugated double bond reacts slower with electrophilic reagents such as m-CPBA
-
12. With time this conjugated double bond could also be epoxidized. A conjugated double bond reacts slower with electrophilic reagents such as m-CPBA.
-
-
-
-
49
-
-
0026665555
-
-
13. This type of epoxide ring opening with silica gel has also been observed by others: Wasserman, H. H.; Prowse, K. S. Tetrahedron Lett. 1992, 33, 5423-5426.
-
(1992)
Tetrahedron Lett.
, vol.33
, pp. 5423-5426
-
-
Wasserman, H.H.1
Prowse, K.S.2
-
50
-
-
19644397969
-
-
14. Corey, E. J.; Gilman, N. W.; Ganem, B. E. J. Am. Chem. Soc. 1968, 90, 5616-5617.
-
(1968)
J. Am. Chem. Soc.
, vol.90
, pp. 5616-5617
-
-
Corey, E.J.1
Gilman, N.W.2
Ganem, B.E.3
-
54
-
-
0001438425
-
-
17. Jenmalm, A.; Berts, W.; Li, Y.-L.; Luthman, K.; Csöregh, I.; Hacksell, U. J. Org. Chem. 1994, 59, 1139-1148.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 1139-1148
-
-
Jenmalm, A.1
Berts, W.2
Li, Y.-L.3
Luthman, K.4
Csöregh, I.5
Hacksell, U.6
-
55
-
-
0026694533
-
-
18. Li, Y.-L.; Luthman, K.; Hacksell, U. Tetrahedron Lett. 1992, 33, 4487-4490.
-
(1992)
Tetrahedron Lett.
, vol.33
, pp. 4487-4490
-
-
Li, Y.-L.1
Luthman, K.2
Hacksell, U.3
-
59
-
-
33751386184
-
-
2 has been reported to activate DAST, see McCarthy, J. R.; Peet, N. P.; LeTourneau, M. E.; Inbasekaran, M. J. Am. Chem. Soc. 1985, 107, 735-737.
-
(1993)
J. Org. Chem.
, vol.58
, pp. 3800-3801
-
-
Robins, M.J.1
Wnuk, S.F.2
-
60
-
-
33845379580
-
-
2 has been reported to activate DAST, see
-
2 has been reported to activate DAST, see McCarthy, J. R.; Peet, N. P.; LeTourneau, M. E.; Inbasekaran, M. J. Am. Chem. Soc. 1985, 107, 735-737.
-
(1985)
J. Am. Chem. Soc.
, vol.107
, pp. 735-737
-
-
McCarthy, J.R.1
Peet, N.P.2
LeTourneau, M.E.3
Inbasekaran, M.4
-
61
-
-
0030027447
-
-
3 to the reaction of 10 from 11 improved the yield from 60% to 83%. However, a corresponding increase in yield was not observed using molecular sieves in the synthesis of 9 from 8. The use of molecular sieves to promote aziridine ring opening reactions has been discussed, see Leung, W.-H.; Yu, M.-T.; Wu, M.-C.; Yeung, L.-L. Tetrahedron Lett. 1996, 37, 891-892.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 891-892
-
-
Leung, W.-H.1
Yu, M.-T.2
Wu, M.-C.3
Yeung, L.-L.4
-
62
-
-
0009521134
-
-
note
-
N2 reaction from the corresponding alcohol with DAST. Thus, the absolute configuration at C-4 in compound 7 in reference 18 should be inverted.
-
-
-
-
63
-
-
45249128736
-
-
and references therein
-
23. For a review on defluorination by hydrogenolysis, see Hudlický, M. J. Fluorine Chem. 1989, 44, 345-359 and references therein.
-
(1989)
J. Fluorine Chem.
, vol.44
, pp. 345-359
-
-
Hudlický, M.1
-
64
-
-
0023685227
-
-
24. Daniewski, A. R.; Kabat, M. M.; Masnyk, M.; Wicha, J.; Wojciechowska, W.; Duddeck, H. J. Org. Chem. 1988, 53, 4855-4858.
-
(1988)
J. Org. Chem.
, vol.53
, pp. 4855-4858
-
-
Daniewski, A.R.1
Kabat, M.M.2
Masnyk, M.3
Wicha, J.4
Wojciechowska, W.5
Duddeck, H.6
-
65
-
-
33947085849
-
-
25. Sharpless, K. B.; Lauer, R. F.; Teranishi, A. Y. J. Am. Chem. Soc. 1973, 95, 6137-6139.
-
(1973)
J. Am. Chem. Soc.
, vol.95
, pp. 6137-6139
-
-
Sharpless, K.B.1
Lauer, R.F.2
Teranishi, A.Y.3
-
66
-
-
0019968012
-
-
Dermorphin
-
26. Dermorphin: Salvadori, S.; Sarto, G.; Tomatis, R. Int. J. Peptide Protein Res. 1982, 19, 536-542. Substance P: Cascieri, M. A.; Huang, R.-R. C.; Fong, T. M.; Cheung, A. H.; Sadowski, S.; Ber, E.; Strader, C. D. Mol. Pharmacol. 1992, 41, 1096-1099.
-
(1982)
Int. J. Peptide Protein Res.
, vol.19
, pp. 536-542
-
-
Salvadori, S.1
Sarto, G.2
Tomatis, R.3
-
67
-
-
0027104212
-
-
Substance P
-
26. Dermorphin: Salvadori, S.; Sarto, G.; Tomatis, R. Int. J. Peptide Protein Res. 1982, 19, 536-542. Substance P: Cascieri, M. A.; Huang, R.-R. C.; Fong, T. M.; Cheung, A. H.; Sadowski, S.; Ber, E.; Strader, C. D. Mol. Pharmacol. 1992, 41, 1096-1099.
-
(1992)
Mol. Pharmacol.
, vol.41
, pp. 1096-1099
-
-
Cascieri, M.A.1
Huang, R.-R.C.2
Fong, T.M.3
Cheung, A.H.4
Sadowski, S.5
Ber, E.6
Strader, C.D.7
-
68
-
-
0000756880
-
-
27. Jenmalm, A.; Berts, W.; Luthman, K.; Csöregh, I.; Hacksell, U. J. Org. Chem. 1995, 60, 1026-1032.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 1026-1032
-
-
Jenmalm, A.1
Berts, W.2
Luthman, K.3
Csöregh, I.4
Hacksell, U.5
-
69
-
-
0001536689
-
-
28. For other methods to synthesize 6 and 7 see: (a) Hanson, G. J.; Lindberg, T. J. Org. Chem. 1985, 50, 5399-5401.
-
(1985)
J. Org. Chem.
, vol.50
, pp. 5399-5401
-
-
Hanson, G.J.1
Lindberg, T.2
-
70
-
-
0000763199
-
-
(b) Ibuka, T.; Habashita, H.; Otaka, A.; Fujii, N.; Oguchi, Y.; Uyehara, T.; Yamamoto, Y. J. Org. Chem. 1991, 56, 4370-4382.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 4370-4382
-
-
Ibuka, T.1
Habashita, H.2
Otaka, A.3
Fujii, N.4
Oguchi, Y.5
Uyehara, T.6
Yamamoto, Y.7
|