-
1
-
-
0033609897
-
-
A. D. Watson, G. Subbanagounder, D. S. Welsbie, K. F. Faull, M. Navab, M. E. Jung, A. M. Fogelman, J. A. Berliner, J. Biol. Chem. 1999, 274, 24787-24798.
-
(1999)
J. Biol. Chem.
, vol.274
, pp. 24787-24798
-
-
Watson, A.D.1
Subbanagounder, G.2
Welsbie, D.S.3
Faull, K.F.4
Navab, M.5
Jung, M.E.6
Fogelman, A.M.7
Berliner, J.A.8
-
2
-
-
17944387960
-
-
a) A. D. Watson, N. Leitinger, M. Navab, K. F. Faull, S. Hörkkö, J. L. Witztum, W. Palinski, D. Schwenke, R. G. Salomon, W. Sha, G. Subbanagounder, A. M. Fogelman, J. A. Berliner, J. Biol. Chem. 1997, 272, 13597-13607;
-
(1997)
J. Biol. Chem.
, vol.272
, pp. 13597-13607
-
-
Watson, A.D.1
Leitinger, N.2
Navab, M.3
Faull, K.F.4
Hörkkö, S.5
Witztum, J.L.6
Palinski, W.7
Schwenke, D.8
Salomon, R.G.9
Sha, W.10
Subbanagounder, G.11
Fogelman, A.M.12
Berliner, J.A.13
-
4
-
-
0037613606
-
-
c) A. Jerlich, R. J. Schaur, A. R. Pitt, C. M. Spickett, Free Radical Res. 2003, 37, 645-653.
-
(2003)
Free Radical Res.
, vol.37
, pp. 645-653
-
-
Jerlich, A.1
Schaur, R.J.2
Pitt, A.R.3
Spickett, C.M.4
-
5
-
-
13044265838
-
-
a) N. Leitinger, T. R. Tyner, L. Oslund, C. Rizza, G. Subbanagounder, H. Lee, P. T. Shih, N. Mackman, G. Tigyi, M. C. Territo, J. A. Berliner, D. K. Vora, Proc. Natl. Acad. Sci. USA 1999, 96, 12010-12015;
-
(1999)
Proc. Natl. Acad. Sci. USA
, vol.96
, pp. 12010-12015
-
-
Leitinger, N.1
Tyner, T.R.2
Oslund, L.3
Rizza, C.4
Subbanagounder, G.5
Lee, H.6
Shih, P.T.7
Mackman, N.8
Tigyi, G.9
Territo, M.C.10
Berliner, J.A.11
Vora, D.K.12
-
6
-
-
0035190081
-
-
b) J. A. Berliner, G. Subbanagounder, N. Leitinger, A. D. Watson, D. Vora, Trends Cardiovasc. Med. 2001, 11, 142-147.
-
(2001)
Trends Cardiovasc. Med.
, vol.11
, pp. 142-147
-
-
Berliner, J.A.1
Subbanagounder, G.2
Leitinger, N.3
Watson, A.D.4
Vora, D.5
-
7
-
-
0032572719
-
-
L. Boring, J. Gosling, M. Cleary, I. F. Charo, Nature 1998, 394, 894-897.
-
(1998)
Nature
, vol.394
, pp. 894-897
-
-
Boring, L.1
Gosling, J.2
Cleary, M.3
Charo, I.F.4
-
8
-
-
0036510551
-
-
G. Subbanagounder, J. W. Wong, H. Lee, K. F. Faull, E. Miller, J. L. Witztum, J. A. Berliner, J. Biol. Chem. 2002, 277, 7271-7281.
-
(2002)
J. Biol. Chem.
, vol.277
, pp. 7271-7281
-
-
Subbanagounder, G.1
Wong, J.W.2
Lee, H.3
Faull, K.F.4
Miller, E.5
Witztum, J.L.6
Berliner, J.A.7
-
9
-
-
0037243077
-
-
M. E. Jung, A. Kers, G. Subbanagounder, J. A. Berliner, Chem. Commun. 2003, 196-197. It is uncertain that the 1,4-addition of the cis-2-heptenyl anion to enone 5 would proceed at the terminal carbon atom of the anion regioselectively with retention of the cis olefin geometry.
-
(2003)
Chem. Commun.
, pp. 196-197
-
-
Jung, M.E.1
Kers, A.2
Subbanagounder, G.3
Berliner, J.A.4
-
10
-
-
2442648083
-
-
For recent reviews of other isoprostane syntheses, see: a) G. Helmchen, M. Ernst, G. Paradies, Pure Appl. Chem. 2004, 76, 495-506;
-
(2004)
Pure Appl. Chem.
, vol.76
, pp. 495-506
-
-
Helmchen, G.1
Ernst, M.2
Paradies, G.3
-
12
-
-
0842287646
-
-
c) T. Durand, A. Guy, O. Henry, A. Roland, S. Bernad, S. E. Fangour, J.-P. Vidal, J.-C. Rossi, Chem. Phys. Lipids 2004, 128, 15-33;
-
(2004)
Chem. Phys. Lipids
, vol.128
, pp. 15-33
-
-
Durand, T.1
Guy, A.2
Henry, O.3
Roland, A.4
Bernad, S.5
Fangour, S.E.6
Vidal, J.-P.7
Rossi, J.-C.8
-
13
-
-
0842346375
-
-
d) J. Rokach, S. Kima, S. Bellone, J. A. Lawson, D. Praticò, W. S. Powell, G. A. FitzGerald, Chem. Phys. Lipids 2004, 128, 35-56;
-
(2004)
Chem. Phys. Lipids
, vol.128
, pp. 35-56
-
-
Rokach, J.1
Kima, S.2
Bellone, S.3
Lawson, J.A.4
Praticò, D.5
Powell, W.S.6
FitzGerald, G.A.7
-
14
-
-
0842346376
-
-
e) D. F. Taber, R. S. Hoerrner, R. J. Herr, D. M. Gleave, K. Kanai, R. Pina, Q. Jiang, M. Xu, Chem. Phys. Lipids 2004, 128, 57-67.
-
(2004)
Chem. Phys. Lipids
, vol.128
, pp. 57-67
-
-
Taber, D.F.1
Hoerrner, R.S.2
Herr, R.J.3
Gleave, D.M.4
Kanai, K.5
Pina, R.6
Jiang, Q.7
Xu, M.8
-
18
-
-
0024987706
-
-
c) M. Suzuki, Y. Morita, H. Koyano, M. Koga, R. Noyori, Tetrahedron 1990, 46, 4809-4822;
-
(1990)
Tetrahedron
, vol.46
, pp. 4809-4822
-
-
Suzuki, M.1
Morita, Y.2
Koyano, H.3
Koga, M.4
Noyori, R.5
-
19
-
-
0023943486
-
-
d) M. Suzuki, T. Kawagishi, A. Yanagisawa, T. Suzuki, N. Okamura, R. Noyori, Bull. Chem. Soc. Jpn. 1988, 61, 1299-1312.
-
(1988)
Bull. Chem. Soc. Jpn.
, vol.61
, pp. 1299-1312
-
-
Suzuki, M.1
Kawagishi, T.2
Yanagisawa, A.3
Suzuki, T.4
Okamura, N.5
Noyori, R.6
-
23
-
-
20444413572
-
-
3-pyridine): A. M. Kornilov, A. E. Sorochinskii, I. A. Butovich, V. P. Kukhar, Zh. Org. Khim. 1987, 23, 2470-2471;
-
(1987)
Zh. Org. Khim.
, vol.23
, pp. 2470-2471
-
-
Kornilov, A.M.1
Sorochinskii, A.E.2
Butovich, I.A.3
Kukhar, V.P.4
-
24
-
-
20444382203
-
-
A. M. Kornilov, A. E. Sorochinskii, I. A. Butovich, V. P. Kukhar, J. Org. Chem. USSR 1987, 23, 2183-2184.
-
(1987)
J. Org. Chem. USSR
, vol.23
, pp. 2183-2184
-
-
Kornilov, A.M.1
Sorochinskii, A.E.2
Butovich, I.A.3
Kukhar, V.P.4
-
25
-
-
0001424829
-
-
a) G. H. Posner, G. M. Gurria, K. A. Babiak, J. Org. Chem. 1977, 42, 3173-3180;
-
(1977)
J. Org. Chem.
, vol.42
, pp. 3173-3180
-
-
Posner, G.H.1
Gurria, G.M.2
Babiak, K.A.3
-
26
-
-
0000429727
-
-
b) K. Yamada, T. Arai, H. Sasai, M. Shibasaki, J. Org. Chem. 1998, 63, 3666-3672.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 3666-3672
-
-
Yamada, K.1
Arai, T.2
Sasai, H.3
Shibasaki, M.4
-
27
-
-
20444366367
-
-
note
-
3-assisted elimination generally produces the thermodynamically stable alkene (see reference [10] and the references cited therein).
-
-
-
-
28
-
-
0020623134
-
-
a) G. L. Bundy, D. R. Morton, D. C. Peterson, E. E. Nishizawa, W. L. Miller, J. Med. Chem. 1983, 26, 790-799;
-
(1983)
J. Med. Chem.
, vol.26
, pp. 790-799
-
-
Bundy, G.L.1
Morton, D.R.2
Peterson, D.C.3
Nishizawa, E.E.4
Miller, W.L.5
-
29
-
-
0021703099
-
-
b) S. Sugiura, T. Toru, T. Tanaka, A. Hazato, N. Okamura, K. Bannai, K. Manabe, S. Kurozumi, R. Noyori, Chem. Pharm. Bull. 1984, 32, 4658-4661;
-
(1984)
Chem. Pharm. Bull.
, vol.32
, pp. 4658-4661
-
-
Sugiura, S.1
Toru, T.2
Tanaka, T.3
Hazato, A.4
Okamura, N.5
Bannai, K.6
Manabe, K.7
Kurozumi, S.8
Noyori, R.9
-
30
-
-
0029036658
-
-
c) J. Zhu, J.-Y. Yang, A. J. H. Klunder, Z.-Y. Liu, B. Zwanenburg, Tetrahedron 1995, 51, 5847-5870.
-
(1995)
Tetrahedron
, vol.51
, pp. 5847-5870
-
-
Zhu, J.1
Yang, J.-Y.2
Klunder, A.J.H.3
Liu, Z.-Y.4
Zwanenburg, B.5
-
31
-
-
20444379087
-
-
note
-
3.
-
-
-
-
32
-
-
20444377459
-
-
note
-
3 set at δ = 7.24 instead of 7.26 ppm).
-
-
-
-
33
-
-
20444417962
-
-
note
-
3) and subsequent lactonization of the resulting diol. (Chemical Equation Presented)
-
-
-
-
35
-
-
0346105709
-
-
b) J. M. Delfino, S. L. Schreiber, F. M. Richards, Tetrahedron Lett. 1987, 28, 2327-2330;
-
(1987)
Tetrahedron Lett.
, vol.28
, pp. 2327-2330
-
-
Delfino, J.M.1
Schreiber, S.L.2
Richards, F.M.3
-
37
-
-
0032741250
-
-
d) F. S. Roodsari, D. Wu, S. G. Pum, J. Hajdu, J. Org. Chem. 1999, 64, 7727-7737;
-
(1999)
J. Org. Chem.
, vol.64
, pp. 7727-7737
-
-
Roodsari, F.S.1
Wu, D.2
Pum, S.G.3
Hajdu, J.4
-
40
-
-
0037059522
-
-
b) J. Lindberg, J. Ekeroth, P. Konradsson, J. Org. Chem. 2002, 67, 194-199;
-
(2002)
J. Org. Chem.
, vol.67
, pp. 194-199
-
-
Lindberg, J.1
Ekeroth, J.2
Konradsson, P.3
-
41
-
-
0037204685
-
-
c) M. Sun, Y. Deng, E. Batyreva, W. Sha, R. G. Salomon, J. Org. Chem. 2002, 67, 3575-3584;
-
(2002)
J. Org. Chem.
, vol.67
, pp. 3575-3584
-
-
Sun, M.1
Deng, Y.2
Batyreva, E.3
Sha, W.4
Salomon, R.G.5
-
42
-
-
20444425991
-
-
d) X. Gu, M. Sun, B. Gugiu, S. Hazen, J. W. Crabb, R. G. Salomon, J. Org. Chem. 2003, 68, 3349-3761; DCC = N,N′-cyclohexylcarbodiimide.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 3349-3761
-
-
Gu, X.1
Sun, M.2
Gugiu, B.3
Hazen, S.4
Crabb, J.W.5
Salomon, R.G.6
-
43
-
-
20444392534
-
-
note
-
2 to afford the product in 77% yield.
-
-
-
-
44
-
-
0001616071
-
-
a) J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993;
-
(1979)
Bull. Chem. Soc. Jpn.
, vol.52
, pp. 1989-1993
-
-
Inanaga, J.1
Hirata, K.2
Saeki, H.3
Katsuki, T.4
Yamaguchi, M.5
-
45
-
-
0030577465
-
-
b) K. Makino, N. Nakajima, S. Hashimoto, O. Yonemitsu, Tetrahedron Lett. 1996, 37, 9077-9080.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 9077-9080
-
-
Makino, K.1
Nakajima, N.2
Hashimoto, S.3
Yonemitsu, O.4
-
46
-
-
0035832085
-
-
We have used the Yamaguchi reagent for the macrocyclization of macrosphelides C, F, G, and H: a) Y. Kobayashi, H. P. Acharya, Tetrahedron Lett. 2001, 42, 2817-2820;
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 2817-2820
-
-
Kobayashi, Y.1
Acharya, H.P.2
-
48
-
-
20444427019
-
-
note
-
Because of the low solubility of the lyso-PC, toluene, the standard solvent for the Yamaguchi reaction, was not used.
-
-
-
-
49
-
-
20444383319
-
-
note
-
Prepared from racemic glycidol according to a literature method; see reference [19b].
-
-
-
|