-
1
-
-
0033518053
-
-
(a) Burke, S. D.; Müller, N.; Beaudry, C. M. Org. Lett. 1999, 1, 1827.
-
(1999)
Org. Lett.
, vol.1
, pp. 1827
-
-
Burke, S.D.1
Müller, N.2
Beaudry, C.M.3
-
3
-
-
0035842153
-
-
(c) Voight, E. A.; Rein, C.; Burke, S. D. Tetrahedron Lett. 2001, 42, 8747.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 8747
-
-
Voight, E.A.1
Rein, C.2
Burke, S.D.3
-
4
-
-
0037195673
-
-
(d) Voight, E. A.; Rein, C.; Burke, S. D. J. Org. Chem. 2002, 67, 8489.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 8489
-
-
Voight, E.A.1
Rein, C.2
Burke, S.D.3
-
5
-
-
0037034310
-
-
Keller, V. A.; Martinelli, J. R.; Strieter, E. R.; Burke, S. D. Org. Lett. 2002, 4, 467.
-
(2002)
Org. Lett.
, vol.4
, pp. 467
-
-
Keller, V.A.1
Martinelli, J.R.2
Strieter, E.R.3
Burke, S.D.4
-
6
-
-
8744274394
-
-
For current information on bryostatin 1 clinical trials, see: http://www.cancer.gov/search/clinical_trials/.
-
-
-
-
7
-
-
0025931117
-
The Bryostatins
-
Herz, W., Ed.; Springer-Verlag: New York
-
For reviews, see: (a) Pettit, G. R. The Bryostatins. In Progress in the Chemistry of Organic Natural Products; Herz, W., Ed.; Springer-Verlag: New York, 1991; Vol. 57, p 153.
-
(1991)
Progress in the Chemistry of Organic Natural Products
, vol.57
, pp. 153
-
-
Pettit, G.R.1
-
10
-
-
0035984562
-
-
(d) Hale, K. J.; Hummersone, M. G.; Manaviazar, S.; Frigerio, M. Nat. Prod. Rep. 2002, 19, 413.
-
(2002)
Nat. Prod. Rep.
, vol.19
, pp. 413
-
-
Hale, K.J.1
Hummersone, M.G.2
Manaviazar, S.3
Frigerio, M.4
-
11
-
-
0037146084
-
-
For analogue studies, see ref 4d and: (a) Wender, P. A.; Baryza, J. L.; Bennett, C. E.; Bi, C.; Brenner, S. E.; Clarke, M. O.; Horan, J. C.; Kan, C.; Lacôte, E.; Lippa, B.; Nell, P. G.; Turner, T. M. J. Am. Chem. Soc. 2002, 124, 13648. (b) Wender, P. A.; Mayweg, A. V. W.; VanDeusen, C. L. Org. Lett. 2003, 5, 277. (c) Hale, K. J.; Frigerio, M.; Manaviazar, S.; Hummersone, M. G.; Fillingham, I. J.; Barsukov, I. G.; Damblon, C. F.; Gescher, A.; Roberts, G. C. K. Org. Lett. 2003, 5, 499.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 13648
-
-
Wender, P.A.1
Baryza, J.L.2
Bennett, C.E.3
Bi, C.4
Brenner, S.E.5
Clarke, M.O.6
Horan, J.C.7
Kan, C.8
Lacôte, E.9
Lippa, B.10
Nell, P.G.11
Turner, T.M.12
-
12
-
-
0013072917
-
-
For analogue studies, see ref 4d and: (a) Wender, P. A.; Baryza, J. L.; Bennett, C. E.; Bi, C.; Brenner, S. E.; Clarke, M. O.; Horan, J. C.; Kan, C.; Lacôte, E.; Lippa, B.; Nell, P. G.; Turner, T. M. J. Am. Chem. Soc. 2002, 124, 13648. (b) Wender, P. A.; Mayweg, A. V. W.; VanDeusen, C. L. Org. Lett. 2003, 5, 277. (c) Hale, K. J.; Frigerio, M.; Manaviazar, S.; Hummersone, M. G.; Fillingham, I. J.; Barsukov, I. G.; Damblon, C. F.; Gescher, A.; Roberts, G. C. K. Org. Lett. 2003, 5, 499.
-
(2003)
Org. Lett.
, vol.5
, pp. 277
-
-
Wender, P.A.1
Mayweg, A.V.W.2
VanDeusen, C.L.3
-
13
-
-
0038683557
-
-
For analogue studies, see ref 4d and: (a) Wender, P. A.; Baryza, J. L.; Bennett, C. E.; Bi, C.; Brenner, S. E.; Clarke, M. O.; Horan, J. C.; Kan, C.; Lacôte, E.; Lippa, B.; Nell, P. G.; Turner, T. M. J. Am. Chem. Soc. 2002, 124, 13648. (b) Wender, P. A.; Mayweg, A. V. W.; VanDeusen, C. L. Org. Lett. 2003, 5, 277. (c) Hale, K. J.; Frigerio, M.; Manaviazar, S.; Hummersone, M. G.; Fillingham, I. J.; Barsukov, I. G.; Damblon, C. F.; Gescher, A.; Roberts, G. C. K. Org. Lett. 2003, 5, 499.
-
(2003)
Org. Lett.
, vol.5
, pp. 499
-
-
Hale, K.J.1
Frigerio, M.2
Manaviazar, S.3
Hummersone, M.G.4
Fillingham, I.J.5
Barsukov, I.G.6
Damblon, C.F.7
Gescher, A.8
Roberts, G.C.K.9
-
14
-
-
0025053566
-
-
Kageyama, M.; Tamura, T.; Nantz, M. H.; Roberts, J. C.; Somfai, P.; Whritenour, D. C.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 7407.
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 7407
-
-
Kageyama, M.1
Tamura, T.2
Nantz, M.H.3
Roberts, J.C.4
Somfai, P.5
Whritenour, D.C.6
Masamune, S.7
-
15
-
-
0033603858
-
-
Evans, D. A.; Carter, P. H.; Carreira, E. M.; Charette, A. B.; Prunet, J. A.; Lautens, M. J. Am. Chem. Soc. 1999, 121, 7540.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 7540
-
-
Evans, D.A.1
Carter, P.H.2
Carreira, E.M.3
Charette, A.B.4
Prunet, J.A.5
Lautens, M.6
-
16
-
-
0034600771
-
-
(a) Ohmori, K.; Ogawa, Y.; Obitsu, T.; Ishikawa, Y.; Nishiyama, S.; Yamamura, S. Angew. Chem., Int. Ed. 2000, 39, 2290.
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 2290
-
-
Ohmori, K.1
Ogawa, Y.2
Obitsu, T.3
Ishikawa, Y.4
Nishiyama, S.5
Yamamura, S.6
-
18
-
-
0037669239
-
-
Hale, K. J.; Frigerio, M.; Manaviazar, S. Org. Lett. 2003, 5, 503.
-
(2003)
Org. Lett.
, vol.5
, pp. 503
-
-
Hale, K.J.1
Frigerio, M.2
Manaviazar, S.3
-
19
-
-
3042697283
-
-
Voight, E. A.; Roethle, P. A.; Burke, S. D. J. Org. Chem. 2004, 69, 4534.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 4534
-
-
Voight, E.A.1
Roethle, P.A.2
Burke, S.D.3
-
21
-
-
24644436103
-
-
The enantiomer of 9 has been prepared previously: Hoffmann, R. W.; Kahrs, B. C.; Schiffer, J.; Fleischhauer, J. J. Chem. Soc., Perkin Trans. 2 1996, 2407. We used D-(-)-diethyltartrate in place of L-(+)-diethyltartrate in the double Sharpless asymmetric epoxidation step of the published sequence to obtain the desired enantiomer.
-
(1996)
J. Chem. Soc., Perkin Trans. 2
, pp. 2407
-
-
Hoffmann, R.W.1
Kahrs, B.C.2
Schiffer, J.3
Fleischhauer, J.4
-
22
-
-
0033523260
-
-
Obtained by treatment of ethyl 4,4-dimethyl-3-oxo-5-hexenoate (b) with (trimethylsilyl)diazomethane (a): (a) Harris, C. R.; Kuduk, S. D.; Balog, A.; Savin, K.; Glunz, P. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 7050. (b) Aurell, M. J.; Gil, S.; Mestres, R.; Parra, M.; Parra, L. Tetrahedron 1998, 54, 4357. (c) Shibuya, M.; Kubota, S. Heterocycles 1980, 14, 601. See the Supporting Information for details.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 7050
-
-
Harris, C.R.1
Kuduk, S.D.2
Balog, A.3
Savin, K.4
Glunz, P.W.5
Danishefsky, S.J.6
-
23
-
-
0032560141
-
-
Obtained by treatment of ethyl 4,4-dimethyl-3-oxo-5-hexenoate (b) with (trimethylsilyl)diazomethane (a): (a) Harris, C. R.; Kuduk, S. D.; Balog, A.; Savin, K.; Glunz, P. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 7050. (b) Aurell, M. J.; Gil, S.; Mestres, R.; Parra, M.; Parra, L. Tetrahedron 1998, 54, 4357. (c) Shibuya, M.; Kubota, S. Heterocycles 1980, 14, 601. See the Supporting Information for details.
-
(1998)
Tetrahedron
, vol.54
, pp. 4357
-
-
Aurell, M.J.1
Gil, S.2
Mestres, R.3
Parra, M.4
Parra, L.5
-
24
-
-
0033523260
-
-
Obtained by treatment of ethyl 4,4-dimethyl-3-oxo-5-hexenoate (b) with (trimethylsilyl)diazomethane (a): (a) Harris, C. R.; Kuduk, S. D.; Balog, A.; Savin, K.; Glunz, P. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 7050. (b) Aurell, M. J.; Gil, S.; Mestres, R.; Parra, M.; Parra, L. Tetrahedron 1998, 54, 4357. (c) Shibuya, M.; Kubota, S. Heterocycles 1980, 14, 601. See the Supporting Information for details.
-
(1980)
Heterocycles
, vol.14
, pp. 601
-
-
Shibuya, M.1
Kubota, S.2
-
25
-
-
3343012187
-
-
For recent reviews, see: (a) Grubbs, R. H. Tetrahedron 2004, 60, 7117. (b) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (d) Schrock, R. R. Tetrahedron 1999, 55, 8141. (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (f) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
-
(2004)
Tetrahedron
, vol.60
, pp. 7117
-
-
Grubbs, R.H.1
-
26
-
-
2942589152
-
-
For recent reviews, see: (a) Grubbs, R. H. Tetrahedron 2004, 60, 7117. (b) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (d) Schrock, R. R. Tetrahedron 1999, 55, 8141. (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (f) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
-
(2004)
Chem. Rev.
, vol.104
, pp. 2199
-
-
Deiters, A.1
Martin, S.F.2
-
27
-
-
0001399412
-
-
For recent reviews, see: (a) Grubbs, R. H. Tetrahedron 2004, 60, 7117. (b) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (d) Schrock, R. R. Tetrahedron 1999, 55, 8141. (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (f) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 3012
-
-
Fürstner, A.1
-
28
-
-
0033516491
-
-
For recent reviews, see: (a) Grubbs, R. H. Tetrahedron 2004, 60, 7117. (b) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (d) Schrock, R. R. Tetrahedron 1999, 55, 8141. (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (f) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
-
(1999)
Tetrahedron
, vol.55
, pp. 8141
-
-
Schrock, R.R.1
-
29
-
-
0032580376
-
-
For recent reviews, see: (a) Grubbs, R. H. Tetrahedron 2004, 60, 7117. (b) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (d) Schrock, R. R. Tetrahedron 1999, 55, 8141. (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (f) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
-
(1998)
Tetrahedron
, vol.54
, pp. 4413
-
-
Grubbs, R.H.1
Chang, S.2
-
30
-
-
28244440935
-
-
For recent reviews, see: (a) Grubbs, R. H. Tetrahedron 2004, 60, 7117. (b) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (d) Schrock, R. R. Tetrahedron 1999, 55, 8141. (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (f) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
-
(1998)
J. Chem. Soc., Perkin Trans. 1
, pp. 371
-
-
Armstrong, S.K.1
-
31
-
-
49549130554
-
-
VanRheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 17, 1973.
-
(1976)
Tetrahedron Lett.
, vol.17
, pp. 1973
-
-
VanRheenen, V.1
Kelly, R.C.2
Cha, D.Y.3
-
33
-
-
0000451948
-
-
Dupau, P.; Epple, R.; Thomas, A. A.; Fokin, V. V.; Sharpless, K. B. Adv. Synth. Catal. 2002, 344, 421. Sharpless has suggested that citric acid assists osmium-catalyzed dihydroxylations by (1) lowering the pH to prevent formation of an essentially inert 18-electron diooxoosmate dianion (which causes the brown color in the original Upjohn process, ref 15) and (2) by preventing Os(VI) disproportionation through bidentate chelation.
-
(2002)
Adv. Synth. Catal.
, vol.344
, pp. 421
-
-
Dupau, P.1
Epple, R.2
Thomas, A.A.3
Fokin, V.V.4
Sharpless, K.B.5
-
34
-
-
0025190551
-
-
Sasaki, M.; Murae, T.; Takahashi, T. J. Org. Chem. 1990, 55, 528.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 528
-
-
Sasaki, M.1
Murae, T.2
Takahashi, T.3
-
35
-
-
0032483567
-
-
Mori, Y.; Yaegashi, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 6200
-
-
Mori, Y.1
Yaegashi, K.2
Furukawa, H.3
-
36
-
-
8744310819
-
-
note
-
See the Supporting Information for details.
-
-
-
-
37
-
-
0028774188
-
-
(a) Lynch, V. M.; Lee, W.-C.; Martin, S. F.; Davis, B. E. Acta Crystallogr. 1994, C50, 1467.
-
(1994)
Acta Crystallogr.
, vol.50 C
, pp. 1467
-
-
Lynch, V.M.1
Lee, W.-C.2
Martin, S.F.3
Davis, B.E.4
-
38
-
-
0001357608
-
-
(b) Peters, J. A.; Baas, J. M. A.; Van de Graaf, B.; Van der Toorn, J. M.; Van Bekkum, H. Tetrahedron 1978, 34, 3313.
-
(1978)
Tetrahedron
, vol.34
, pp. 3313
-
-
Peters, J.A.1
Baas, J.M.A.2
Van De Graaf, B.3
Van Der Toorn, J.M.4
Van Bekkum, H.5
-
39
-
-
0035132214
-
-
(a) Martín, M.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. Synlett 2001, 117.
-
(2001)
Synlett
, pp. 117
-
-
Martín, M.1
Afonso, M.M.2
Galindo, A.3
Palenzuela, J.A.4
-
40
-
-
0032567409
-
-
(b) Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. J. Org. Chem. 1998, 63, 9728.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 9728
-
-
Mujica, M.T.1
Afonso, M.M.2
Galindo, A.3
Palenzuela, J.A.4
-
42
-
-
0019964601
-
-
(d) Danishefsky, S. J.; Kobayashi, S.; Kerwin, J. F. J. Org. Chem. 1982, 47, 1981.
-
(1982)
J. Org. Chem.
, vol.47
, pp. 1981
-
-
Danishefsky, S.J.1
Kobayashi, S.2
Kerwin, J.F.3
-
43
-
-
8744228174
-
-
note
-
A product with TBDPS and pentylidene ketal still present could be isolated in 55% yield after 1 h, 45 min under these conditions.
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