-
1
-
-
0034108155
-
-
Sam, T. W.; Yeu, C. S.; Jodynis-Liebert, J.; Murias, M.; Bloszyk, E. Planta Med. 2000, 66, 199.
-
(2000)
Planta Med.
, vol.66
, pp. 199
-
-
Sam, T.W.1
Yeu, C.S.2
Jodynis-Liebert, J.3
Murias, M.4
Bloszyk, E.5
-
3
-
-
0000330039
-
-
(a) Drewes, S. E.; Schlapelo, B. M.; Horn, M. M.; Scott-Shaw, R.; Sandor, O. Phytochemistry 1995, 38, 1427.
-
(1995)
Phytochemistry
, vol.38
, pp. 1427
-
-
Drewes, S.E.1
Schlapelo, B.M.2
Horn, M.M.3
Scott-Shaw, R.4
Sandor, O.5
-
4
-
-
0031106672
-
-
(b) Collett, L. A.; Cavies-Coleman, M. T.; Rivett, D. E. A.; Drewes, S. E.; Horn, M. M. Phytochemistry 1997, 44, 935.
-
(1997)
Phytochemistry
, vol.44
, pp. 935
-
-
Collett, L.A.1
Cavies-Coleman, M.T.2
Rivett, D.E.A.3
Drewes, S.E.4
Horn, M.M.5
-
5
-
-
0032869162
-
-
Andrianaivoravelona, J. O.; Sahpaz, S.; Terreaux, C.; Hostettmann, K.; Stoecki-Evans, H.; Rasolondramanitra, J. Phytochemistry 1999, 52, 265.
-
(1999)
Phytochemistry
, vol.52
, pp. 265
-
-
Andrianaivoravelona, J.O.1
Sahpaz, S.2
Terreaux, C.3
Hostettmann, K.4
Stoecki-Evans, H.5
Rasolondramanitra, J.6
-
6
-
-
0035849139
-
-
(a) Echeverri, F.; Arango, V.; Quinones, W.; Torres, F.; Escobar, G.; Rosero, Y.; Archbold, R. Phytochemistry 2001, 56, 881.
-
(2001)
Phytochemistry
, vol.56
, pp. 881
-
-
Echeverri, F.1
Arango, V.2
Quinones, W.3
Torres, F.4
Escobar, G.5
Rosero, Y.6
Archbold, R.7
-
8
-
-
0034108155
-
-
(a) Jodynis-Liebert, J.; Murias, M.; Bloszyk, E. Planta Med. 2000, 66, 199.
-
(2000)
Planta Med.
, vol.66
, pp. 199
-
-
Jodynis-Liebert, J.1
Murias, M.2
Bloszyk, E.3
-
9
-
-
0019946724
-
-
(b) Meyer, B. N.; Ferrigni, N. R.; Putnam, J. E.; Jacobsen, L. B.; Nicholson, D. E. Planta Med. 1982, 45, 31.
-
(1982)
Planta Med.
, vol.45
, pp. 31
-
-
Meyer, B.N.1
Ferrigni, N.R.2
Putnam, J.E.3
Jacobsen, L.B.4
Nicholson, D.E.5
-
10
-
-
0000330039
-
-
Drewes, S. E.; Schlapelo, B. M.; Horn, M. M.; Scott-Shaw, R.; Sandor, O. Phytochemistry 1995, 38, 1427.
-
(1995)
Phytochemistry
, vol.38
, pp. 1427
-
-
Drewes, S.E.1
Schlapelo, B.M.2
Horn, M.M.3
Scott-Shaw, R.4
Sandor, O.5
-
12
-
-
0037134222
-
-
(b) Garaas, S.; Hunter, T. J.; O'Doherty, G. A. J. Org. Chem. 2002, 67 (8), 2682.
-
(2002)
J. Org. Chem.
, vol.67
, Issue.8
, pp. 2682
-
-
Garaas, S.1
Hunter, T.J.2
O'Doherty, G.A.3
-
13
-
-
0000480096
-
-
(a) Nakata, T.; Hata, N.; Iida, K.; Oishi, T. Tetrahedron Lett. 1987, 28, 5661.
-
(1987)
Tetrahedron Lett.
, vol.28
, pp. 5661
-
-
Nakata, T.1
Hata, N.2
Iida, K.3
Oishi, T.4
-
15
-
-
0025110148
-
-
(c) Mori, Y.; Kageyama, H.; Suzuki, M. Chem. Pharm. Bull. 1990, 38, 2574.
-
(1990)
Chem. Pharm. Bull.
, vol.38
, pp. 2574
-
-
Mori, Y.1
Kageyama, H.2
Suzuki, M.3
-
17
-
-
0033544814
-
-
(e) Jorgensen, K. B.; Suenaga, T.; Nakata, T. Tetrahedron Lett. 1999, 40, 8855.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 8855
-
-
Jorgensen, K.B.1
Suenaga, T.2
Nakata, T.3
-
18
-
-
0035815129
-
-
(f) Reddy, M. V. R.; Yucel, A. J.; Ramachandran, P. V. J. Org. Chem. 2001, 66, 2512.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 2512
-
-
Reddy, M.V.R.1
Yucel, A.J.2
Ramachandran, P.V.3
-
20
-
-
0034800738
-
-
(h) Boger, D. L.; Ichikawa, D.; Zhong, W. J. Am. Chem. Soc. 2001, 123, 4161.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 4161
-
-
Boger, D.L.1
Ichikawa, D.2
Zhong, W.3
-
21
-
-
0035843312
-
-
(i) Reddy, M. V. R.; Rearick, J. P.; Hoch, N.; Ramachandran, P. V. Org. Lett. 2001, 3, 19.
-
(2001)
Org. Lett.
, vol.3
, pp. 19
-
-
Reddy, M.V.R.1
Rearick, J.P.2
Hoch, N.3
Ramachandran, P.V.4
-
23
-
-
0033544814
-
-
Jorgensen, K. B.; Suenaga, T.; Nakata, T. Tetrahedron Lett. 1999, 40, 8855.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 8855
-
-
Jorgensen, K.B.1
Suenaga, T.2
Nakata, T.3
-
24
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0141490440
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note
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Aldrich Chemical Co. provides (S)-tert-butyl 3-hydroxybutyrate at the cost of $41/mL.
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25
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0141825078
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note
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At the outset of this project, we set the goal for efficiency as three steps/stereocenter of the target molecule.
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26
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0000417893
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-
Also see, ref 8
-
Hunter, T. J.; O'Doherty, G. A. Org. Lett. 2001, 3 (17), 1049. Also see, ref 8.
-
(2001)
Org. Lett.
, vol.3
, Issue.17
, pp. 1049
-
-
Hunter, T.J.1
O'Doherty, G.A.2
-
27
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0141713736
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note
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We have found that for the successful implementation of the Evans acetal-forming reaction, the δ-hydroxy-1-enoates must be in their trans form to prevent lactonization.
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28
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0042790515
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For vinylogous aldol approaches to δ-hydroxy-1-enoates, see: (a) Fleming, I. Bull. Soc. Chem. Fr. 1981, 2, 7. (b) Barloy-Da Silva, C.; Benkouider, A.; Pale, P. Tetrahedron Lett. 2000, 41, 3077. (c) Albaugh-Robertson, P.; Katzenellenbogen, J. A. J. Org. Chem. 1983, 48, 5288. For aldol/Wittig approaches, see ref 16 and: (d) Keck, G. E.; Palani, A.; McHardy, S. F. J. Org. Chem. 1994, 59, 3113. (e) Solladie, G.; Gressot, L.; Colobert, F. Eur. J. Org. Chem. 2000, 357.
-
(1981)
Bull. Soc. Chem. Fr.
, vol.2
, pp. 7
-
-
Fleming, I.1
-
29
-
-
0034701459
-
-
For vinylogous aldol approaches to δ-hydroxy-1-enoates, see: (a) Fleming, I. Bull. Soc. Chem. Fr. 1981, 2, 7. (b) Barloy-Da Silva, C.; Benkouider, A.; Pale, P. Tetrahedron Lett. 2000, 41, 3077. (c) Albaugh-Robertson, P.; Katzenellenbogen, J. A. J. Org. Chem. 1983, 48, 5288. For aldol/Wittig approaches, see ref 16 and: (d) Keck, G. E.; Palani, A.; McHardy, S. F. J. Org. Chem. 1994, 59, 3113. (e) Solladie, G.; Gressot, L.; Colobert, F. Eur. J. Org. Chem. 2000, 357.
-
(2000)
Tetrahedron Lett.
, vol.41
, pp. 3077
-
-
Barloy-Da Silva, C.1
Benkouider, A.2
Pale, P.3
-
30
-
-
0042289410
-
-
For vinylogous aldol approaches to δ-hydroxy-1-enoates, see: (a) Fleming, I. Bull. Soc. Chem. Fr. 1981, 2, 7. (b) Barloy-Da Silva, C.; Benkouider, A.; Pale, P. Tetrahedron Lett. 2000, 41, 3077. (c) Albaugh-Robertson, P.; Katzenellenbogen, J. A. J. Org. Chem. 1983, 48, 5288. For aldol/Wittig approaches, see ref 16 and: (d) Keck, G. E.; Palani, A.; McHardy, S. F. J. Org. Chem. 1994, 59, 3113. (e) Solladie, G.; Gressot, L.; Colobert, F. Eur. J. Org. Chem. 2000, 357.
-
(1983)
J. Org. Chem.
, vol.48
, pp. 5288
-
-
Albaugh-Robertson, P.1
Katzenellenbogen, J.A.2
-
31
-
-
0001088883
-
-
For vinylogous aldol approaches to δ-hydroxy-1-enoates, see: (a) Fleming, I. Bull. Soc. Chem. Fr. 1981, 2, 7. (b) Barloy-Da Silva, C.; Benkouider, A.; Pale, P. Tetrahedron Lett. 2000, 41, 3077. (c) Albaugh-Robertson, P.; Katzenellenbogen, J. A. J. Org. Chem. 1983, 48, 5288. For aldol/Wittig approaches, see ref 16 and: (d) Keck, G. E.; Palani, A.; McHardy, S. F. J. Org. Chem. 1994, 59, 3113. (e) Solladie, G.; Gressot, L.; Colobert, F. Eur. J. Org. Chem. 2000, 357.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 3113
-
-
Keck, G.E.1
Palani, A.2
McHardy, S.F.3
-
32
-
-
0033955120
-
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For vinylogous aldol approaches to δ-hydroxy-1-enoates, see: (a) Fleming, I. Bull. Soc. Chem. Fr. 1981, 2, 7. (b) Barloy-Da Silva, C.; Benkouider, A.; Pale, P. Tetrahedron Lett. 2000, 41, 3077. (c) Albaugh-Robertson, P.; Katzenellenbogen, J. A. J. Org. Chem. 1983, 48, 5288. For aldol/Wittig approaches, see ref 16 and: (d) Keck, G. E.; Palani, A.; McHardy, S. F. J. Org. Chem. 1994, 59, 3113. (e) Solladie, G.; Gressot, L.; Colobert, F. Eur. J. Org. Chem. 2000, 357.
-
(2000)
Eur. J. Org. Chem.
, pp. 357
-
-
Solladie, G.1
Gressot, L.2
Colobert, F.3
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33
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0026658420
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For examples of the Wittig approach to trans-δ-hydroxy-1-enoates from homoallylic alcohols, see: Diez-Martin, D.; Kotecha, N. R.; Ley, S. V.; Mantegani, S.; Menendez, C. J. Tetrahedron 1992, 48 (37), 7899.
-
(1992)
Tetrahedron
, vol.48
, Issue.37
, pp. 7899
-
-
Diez-Martin, D.1
Kotecha, N.R.2
Ley, S.V.3
Mantegani, S.4
Menendez, C.J.5
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34
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0035902255
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As this methodology was being completed, Cossy reported similar cross-metathesis acetyl-protected homoallylic alcohols and enoates; see: (a) BouzBouz, S.; Cossy, J. Org. Lett. 2001, 3, 1451. (b) Cossy, J.; Bargiggia, F.; BouzBouz, S. Org. Lett. 2003, 5, 459. For a related example, see: (c) Dreher, S. D.; Leighton, J. L. J. Am. Chem. Soc. 2001, 123, 341.
-
(2001)
Org. Lett.
, vol.3
, pp. 1451
-
-
BouzBouz, S.1
Cossy, J.2
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35
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0141451922
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As this methodology was being completed, Cossy reported similar cross-metathesis acetyl-protected homoallylic alcohols and enoates; see: (a) BouzBouz, S.; Cossy, J. Org. Lett. 2001, 3, 1451. (b) Cossy, J.; Bargiggia, F.; BouzBouz, S. Org. Lett. 2003, 5, 459. For a related example, see: (c) Dreher, S. D.; Leighton, J. L. J. Am. Chem. Soc. 2001, 123, 341.
-
(2003)
Org. Lett.
, vol.5
, pp. 459
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-
Cossy, J.1
Bargiggia, F.2
BouzBouz, S.3
-
36
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0035900986
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As this methodology was being completed, Cossy reported similar cross-metathesis acetyl-protected homoallylic alcohols and enoates; see: (a) BouzBouz, S.; Cossy, J. Org. Lett. 2001, 3, 1451. (b) Cossy, J.; Bargiggia, F.; BouzBouz, S. Org. Lett. 2003, 5, 459. For a related example, see: (c) Dreher, S. D.; Leighton, J. L. J. Am. Chem. Soc. 2001, 123, 341.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 341
-
-
Dreher, S.D.1
Leighton, J.L.2
-
38
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0034685462
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(a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 3783
-
-
Chatterjee, A.K.1
Morgan, J.P.2
Scholl, M.3
Grubbs, R.H.4
-
39
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0035794963
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(b) Choi, T. L.; Chatterjee, A. K.; Grubbs, R. H. Angew. Chem., Int. Ed. 2001, 40, 1277.
-
(2001)
Angew. Chem., Int. Ed.
, vol.40
, pp. 1277
-
-
Choi, T.L.1
Chatterjee, A.K.2
Grubbs, R.H.3
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40
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0141601973
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note
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1H NMR analysis (at 500 MHz).
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41
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0141490439
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note
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13C NMR, FTIR, HRMS, and/or elemental analysis.
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42
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0141825077
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note
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This result was somewhat surprising given that Grubbs et al. have shown that ω-hydroxy-α-olefins smoothly undergo the cross-coupling reaction with the Weinreb amide of acrylic acid; see ref 19.
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0034728153
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For other approaches to pyranone synthesis, see refs 8b and 9d and: (a) Hayakawa, H.; Miyashita, M. Tetrahedron Lett. 2000, 41, 707. (b) Tosaki, S.-Y.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Org. Lett. 2003, 5, 495.
-
(2000)
Tetrahedron Lett.
, vol.41
, pp. 707
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Hayakawa, H.1
Miyashita, M.2
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45
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0038496699
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For other approaches to pyranone synthesis, see refs 8b and 9d and: (a) Hayakawa, H.; Miyashita, M. Tetrahedron Lett. 2000, 41, 707. (b) Tosaki, S.-Y.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Org. Lett. 2003, 5, 495.
-
(2003)
Org. Lett.
, vol.5
, pp. 495
-
-
Tosaki, S.-Y.1
Nemoto, T.2
Ohshima, T.3
Shibasaki, M.4
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