-
1
-
-
0024501805
-
-
Isolation and properties: a) N. Andres, H. Wolf, H. Zähner, E. Rössner, A. Zeeck, W. A. König, V. Sinnwell, Helv. Chim. Acta 1989, 72, 426-437;
-
(1989)
Helv. Chim. Acta
, vol.72
, pp. 426-437
-
-
Andres, N.1
Wolf, H.2
Zähner, H.3
Rössner, E.4
Zeeck, A.5
König, W.A.6
Sinnwell, V.7
-
2
-
-
0012305750
-
-
b) E. Rössner, A. Zeeck, W. A. König, Angew. Chem. 1990, 102, 84-85; Angew. Chem. Int. Ed. Engl. 1990, 29, 64-65;
-
(1990)
Angew. Chem.
, vol.102
, pp. 84-85
-
-
Rössner, E.1
Zeeck, A.2
König, W.A.3
-
3
-
-
0012318137
-
-
b) E. Rössner, A. Zeeck, W. A. König, Angew. Chem. 1990, 102, 84-85; Angew. Chem. Int. Ed. Engl. 1990, 29, 64-65;
-
(1990)
Angew. Chem. Int. Ed. Engl.
, vol.29
, pp. 64-65
-
-
-
4
-
-
0345382021
-
-
c) K. Otoguro, H. Ui, A. Ishiyama, N. Arai, M. Kobayashi, Y. Takahashi, R. Masuma, K. Shiomi, H. Yamada, S. Omura, J. Antibiotics 2003, 56, 322-324.
-
(2003)
J. Antibiotics
, vol.56
, pp. 322-324
-
-
Otoguro, K.1
Ui, H.2
Ishiyama, A.3
Arai, N.4
Kobayashi, M.5
Takahashi, Y.6
Masuma, R.7
Shiomi, K.8
Yamada, H.9
Omura, S.10
-
6
-
-
5444246119
-
-
Final structure elucidation: e) B. Zlatopolskiy, K. Loscha, P. Alvermann, S. I. Kozhushkov, S. V. Nikolaev, A. Zeeck, A. de Meijere, Chem. Eur. J. 2004, 10, 4708-4717.
-
(2004)
Chem. Eur. J.
, vol.10
, pp. 4708-4717
-
-
Zlatopolskiy, B.1
Loscha, K.2
Alvermann, P.3
Kozhushkov, S.I.4
Nikolaev, S.V.5
Zeeck, A.6
De Meijere, A.7
-
7
-
-
9244260150
-
-
The formula of 1a as presented here and in these previous publications do depict the correct configuration in the (S)-isoleucine (He) moiety. The formulas in our recently published "Corrigendum" (see Chem. Eur. J. 2004, 10, 5568) were indeed erroneous in this respect.
-
(2004)
Chem. Eur. J.
, vol.10
, pp. 5568
-
-
-
8
-
-
0033981105
-
-
Isolation and properties: a) A. Asai, A. Hasegawa, K. Ochiai, Y. Yamashita, T. Mizukami, J. Antibiotics 2000, 53, 81-83;
-
(2000)
J. Antibiotics
, vol.53
, pp. 81-83
-
-
Asai, A.1
Hasegawa, A.2
Ochiai, K.3
Yamashita, Y.4
Mizukami, T.5
-
9
-
-
3142670502
-
-
Eur. Patent 1, 166, 781 A1 2000
-
b) H. Yamaguchi, A. Asai, T. Mizukami, Y. Yamashita, S. Akinaga, S.-i. Ikeda, Y. Kanda, Eur. Patent 1, 166, 781 A1 2000; Chem. Abstr. 2000, 133, 751;
-
(2000)
Chem. Abstr.
, vol.133
, pp. 751
-
-
Yamaguchi, H.1
Asai, A.2
Mizukami, T.3
Yamashita, Y.4
Akinaga, S.5
Ikeda, S.-I.6
Kanda, Y.7
-
10
-
-
1642276251
-
-
c) A. Asai, T. Tsujita, S. V. Sharma, Y. Yamashita, S. Akinaga, M. Funakoshi, H. Kobayashi, T. Mizukami, M.-s. Asahi-machi, Biochem. Pharmacol. 2004, 67, 227-234.
-
(2004)
Biochem. Pharmacol.
, vol.67
, pp. 227-234
-
-
Asai, A.1
Tsujita, T.2
Sharma, S.V.3
Yamashita, Y.4
Akinaga, S.5
Funakoshi, M.6
Kobayashi, H.7
Mizukami, T.8
Asahi-Machi, M.-S.9
-
13
-
-
0037338374
-
-
Preparations of the non-labeled enantiomerically pure 3-(trans-2′-nitrocyclopropyl)alanines (3): a) O. V. Larionov, T. F. Savelieva, K. A. Kochetkov, N. S. Ikonnokov, S. I. Kozhushkov, D. S. Yufit, J. A. K. Howard, V. N. Khrustalev, Yu. N. Belokon, A. de Meijere, Eur. J. Org. Chem. 2003, 869-877.
-
(2003)
Eur. J. Org. Chem.
, pp. 869-877
-
-
Larionov, O.V.1
Savelieva, T.F.2
Kochetkov, K.A.3
Ikonnokov, N.S.4
Kozhushkov, S.I.5
Yufit, D.S.6
Howard, J.A.K.7
Khrustalev, V.N.8
Belokon, Y.N.9
De Meijere, A.10
-
14
-
-
0027416890
-
-
For the synthesis of enantiomerically pure mixtures of epimers of 3 see also: b) J. Zindel, A. Zeeck, W. A. König, A. de Meijere, Tetrahedron Lett. 1993, 34, 1917-1920;
-
(1993)
Tetrahedron Lett.
, vol.34
, pp. 1917-1920
-
-
Zindel, J.1
Zeeck, A.2
König, W.A.3
De Meijere, A.4
-
17
-
-
15044349562
-
-
Dissertation, University of Göttingen
-
e) J. Zindel, Dissertation, University of Göttingen, 1993.
-
(1993)
-
-
Zindel, J.1
-
18
-
-
0034536121
-
-
Preliminary communication: a) M. Brandi, S. I. Kozhushkov, K. Loscha, O. V. Kokoreva, D. S. Yufit, J. A. K. Howard, A. de Meijere, Synlett 2000, 1741-1744.
-
(2000)
Synlett
, pp. 1741-1744
-
-
Brandi, M.1
Kozhushkov, S.I.2
Loscha, K.3
Kokoreva, O.V.4
Yufit, D.S.5
Howard, J.A.K.6
De Meijere, A.7
-
19
-
-
0141853177
-
-
This strategy was recently applied for the preparation of enantiomerically pure 4, which in turn was used in the total synthesis of 2 (see ref. [2e]); b) A. Armstrong, J. N. Scutt, Org. Lett. 2003, 5, 2331-2334.
-
(2003)
Org. Lett.
, vol.5
, pp. 2331-2334
-
-
Armstrong, A.1
Scutt, J.N.2
-
20
-
-
0344628717
-
-
For an alternative approach to 4 see also: c) O. V. Larionov, S. I. Kozhushkov, M. Brandl, A. de Meijere, Mendeleev Commun. 2003, 199-200.
-
(2003)
Mendeleev Commun.
, pp. 199-200
-
-
Larionov, O.V.1
Kozhushkov, S.I.2
Brandl, M.3
De Meijere, A.4
-
21
-
-
0026386768
-
-
The amino acid 5 has previously been prepared in four steps starting from 2-amino-4-pentenoic acid with an overall yield of only 44%. It has been shown to be a selective partial agonist of the N-methyl-D-aspartate (NMDA) receptor site: R. Pellicciari, B. Natalini, M. Marinozzi, B. M. Sadeghpour, A. A. Cordi, T. H. Lanthorn, W. F. Hood, J. B. Monahan, Farmaco 1991, 46, 1243-1264.
-
(1991)
Farmaco
, vol.46
, pp. 1243-1264
-
-
Pellicciari, R.1
Natalini, B.2
Marinozzi, M.3
Sadeghpour, B.M.4
Cordi, A.A.5
Lanthorn, T.H.6
Hood, W.F.7
Monahan, J.B.8
-
22
-
-
0029985979
-
-
and references cited therein
-
a) C. Hamon, B. J. Rawlings, Synth. Commun. 1996, 26, 1109-1116, and references cited therein.
-
(1996)
Synth. Commun.
, vol.26
, pp. 1109-1116
-
-
Hamon, C.1
Rawlings, B.J.2
-
23
-
-
0000234063
-
-
This compound was prepared by alkylation of the lithiated O'Donnel's glycine equivalent 11 with iodomethylcyclopropane followed by acid-catalyzed deprotection, see also: b) E. J. Corey, F. Xu, M. C. Noe, J. Am. Chem. Soc. 1997, 119, 12414-12415;
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 12414-12415
-
-
Corey, E.J.1
Xu, F.2
Noe, M.C.3
-
25
-
-
0021062284
-
-
E. J. Corey, S. G. Pyne, W. Su, Tetrahedron Lett. 1983, 24, 4883-4886.
-
(1983)
Tetrahedron Lett.
, vol.24
, pp. 4883-4886
-
-
Corey, E.J.1
Pyne, S.G.2
Su, W.3
-
27
-
-
0002076066
-
-
and ref.[3] cited therein
-
b) for recent reviews see: M. J. O'Donnell, Aldrichimica Acta 2001, 34, 3-15, and ref.[3] cited therein.
-
(2001)
Aldrichimica Acta
, vol.34
, pp. 3-15
-
-
O'Donnell, M.J.1
-
28
-
-
0029010820
-
-
Several of the conceivable approaches to 4 such as the Curtius degradation of protected 3-(trans-2-hydroxycarbonylcyclopropyl)alanine as well as substitution of the 3-[trans-2-(tert-butoxycarbonyl)aminocyclopropyl]methanol tosylate with the nucleophilic O'Donnell glycine equivalent 11 were tested without any success. The starting materials for these attempted transformations were prepared from dimethyl trans-1,2-cyclopropanedicarboxylate according to published procedures. Cf. a) R. Csuk, Y. v. Scholz, Tetrahedron 1995, 51, 7193-7206;
-
(1995)
Tetrahedron
, vol.51
, pp. 7193-7206
-
-
Csuk, R.1
Scholz, Y.V.2
-
31
-
-
33744586503
-
-
b) N. Miyashita, A. Yoshikoshi, P. A. Greico, J. Org. Chem. 1977, 42, 3772-3774;
-
(1977)
J. Org. Chem.
, vol.42
, pp. 3772-3774
-
-
Miyashita, N.1
Yoshikoshi, A.2
Greico, P.A.3
-
32
-
-
0001340433
-
-
c) G. Kokotos, J. M. Padron, T. Martin, W. A. Gibbons, V. S. Martin, J. Org. Chem. 1998, 63, 3741-3744;
-
(1998)
J. Org. Chem.
, vol.63
, pp. 3741-3744
-
-
Kokotos, G.1
Padron, J.M.2
Martin, T.3
Gibbons, W.A.4
Martin, V.S.5
-
33
-
-
84987460643
-
-
d) G. Bold, H. Steiner, L. Moesch, B. Walliser, Helv. Chim. Acta 1990, 73, 405-410.
-
(1990)
Helv. Chim. Acta
, vol.73
, pp. 405-410
-
-
Bold, G.1
Steiner, H.2
Moesch, L.3
Walliser, B.4
-
36
-
-
37049066755
-
-
c) D. P. Curran, J. Xu, E. Lazzarini, J. Chem. Soc. Perkin Trans. 1 Chem. Soc. Perkin Trans, 1 1995, 3049-3060;
-
(1995)
J. Chem. Soc. Perkin Trans. 1 Chem. Soc. Perkin Trans, 1
, pp. 3049-3060
-
-
Curran, D.P.1
Xu, J.2
Lazzarini, E.3
-
39
-
-
11844294079
-
-
M. Brandl, S. I. Kozhushkov, B. Zlatopolskiy, P. Alvermann, B. Geers, A. Zeeck, A. de Meijere, Eur. J. Org. Chem. 2005, 123-135.
-
(2005)
Eur. J. Org. Chem.
, pp. 123-135
-
-
Brandl, M.1
Kozhushkov, S.I.2
Zlatopolskiy, B.3
Alvermann, P.4
Geers, B.5
Zeeck, A.6
De Meijere, A.7
-
40
-
-
15044351261
-
-
Dissertation, University of Göttingen
-
For experimental details see: P. Alvermann, Dissertation, University of Göttingen, 2001.
-
(2001)
-
-
Alvermann, P.1
-
41
-
-
0001296027
-
-
H. von Döhren, U. Keller, J. Vater, R. Zocher, Chem. Rev. 1997, 97, 2675-2705.
-
(1997)
Chem. Rev.
, vol.97
, pp. 2675-2705
-
-
Von Döhren, H.1
Keller, U.2
Vater, J.3
Zocher, R.4
-
43
-
-
15044347479
-
-
note
-
1H-NMR spectra. Moreover, at least for one hormaomycin analogue, 1H-NMR spectra measured with the same spectrometer, in the same solvent, at the same temperature, and from the same sample showed distinct differences. See ref.[1d] for a deeper discussion.
-
-
-
-
44
-
-
0000072258
-
-
(Ed.: P. de Mayo), Academic Press, New York
-
a) A. L. J. Beckwith, K. U. Ingold, in: Rearrangements in Ground and Excited States, vol. 1 (Ed.: P. de Mayo), Academic Press, New York, 1980, pp. 161-310;
-
(1980)
Rearrangements in Ground and Excited States
, vol.1
, pp. 161-310
-
-
Beckwith, A.L.J.1
Ingold, K.U.2
-
45
-
-
0041812777
-
-
(Ed.: A. de Meijere), Thieme, Stuttgart
-
b) J. C. Walton, in Methods of Organic Chemistry (Houben-Weyl), vol. E17c (Ed.: A. de Meijere), Thieme, Stuttgart, 1997, pp. 2438-2525.
-
(1997)
Methods of Organic Chemistry (Houben-Weyl)
, vol.E17C
, pp. 2438-2525
-
-
Walton, J.C.1
-
46
-
-
2742566089
-
-
(Ed.: E. Müller), Thieme, Stuttgart
-
a) D. Wendisch, in: Methoden der Organischen Chemie (Houben-Weyl), vol. 4/3 (Ed.: E. Müller), Thieme, Stuttgart, 1971, pp. 399-405;
-
(1971)
Methoden der Organischen Chemie (Houben-Weyl)
, vol.4
, Issue.3
, pp. 399-405
-
-
Wendisch, D.1
-
47
-
-
0003471628
-
-
(Eds.: S. Patai, Z. Rappoport), Wiley, Chichester, and references therein
-
c) G. Boche, H. M. Walborsky, Cyclopropane-Derived Reactive Intermediates (Eds.: S. Patai, Z. Rappoport), Wiley, Chichester, 1990, and references therein.
-
(1990)
Cyclopropane-Derived Reactive Intermediates
-
-
Boche, G.1
Walborsky, H.M.2
-
48
-
-
0000776069
-
-
a) M.-t. Lai, L.-d. Liu, H.-w. Liu, J. Am. Chem. Soc. 1991, 113, 7388-7397;
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 7388-7397
-
-
Lai, M.-T.1
Liu, L.-D.2
Liu, H.-W.3
-
50
-
-
9444278428
-
-
M. A. Marahiel, T. Stachelhaus, H. D. Mootz, Chem. Rev. 1997, 97, 2651-2673.
-
(1997)
Chem. Rev.
, vol.97
, pp. 2651-2673
-
-
Marahiel, M.A.1
Stachelhaus, T.2
Mootz, H.D.3
-
51
-
-
15044360753
-
-
note
-
In the radical homoallylic rearrangement of hypoglycine A the arising intermediate inactivates general Acyl-CoA Dehydrogenase, see ref.[20]
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-
-
-
52
-
-
15044364662
-
-
in press
-
U. M. Reinscheid, B. D. Zlatopolskiy, A. Zeeck, C. Griesinger, A. de Meijere, Chem. Eur. J., in press.
-
Chem. Eur. J.
-
-
Reinscheid, U.M.1
Zlatopolskiy, B.D.2
Zeeck, A.3
Griesinger, C.4
De Meijere, A.5
-
53
-
-
0034611326
-
-
For the synthesis of the starting di- and monomethyl esters of trans-cyclopropane-1,2-dicarboxylic acid, the protocol of Csuk et al. (ref.[9b]) was used. See also: K. M. Edvinsson, M. Hersloef, P. Holm, N. Kann, D. J. Keeling, J. P. Mattsson, B. Norden, V. Shcherbukhin, Bioorg. Med. Chem. Lett. 2000, 10, 503-508.
-
(2000)
Bioorg. Med. Chem. Lett.
, vol.10
, pp. 503-508
-
-
Edvinsson, K.M.1
Hersloef, M.2
Holm, P.3
Kann, N.4
Keeling, D.J.5
Mattsson, J.P.6
Norden, B.7
Shcherbukhin, V.8
-
54
-
-
15044357327
-
-
note
-
a) For spectroscopic and analytical data of the non-deuterated compound see refs.[3d,4];
-
-
-
-
55
-
-
0028220912
-
-
b) for another method of preparation of a non-deuterated compound see also: L. Dechoux, E. Doris, Tetrahedron Lett. 1994, 35, 2017-2020.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 2017-2020
-
-
Dechoux, L.1
Doris, E.2
-
56
-
-
15044354826
-
-
note
-
a) For spectroscopic and analytical data of the non-deuterated compound see refs.[3e,9a];
-
-
-
-
57
-
-
15044365970
-
-
note
-
b) for another method of preparation of the non-deuterated compound see refs.[9a,9b]
-
-
-
-
58
-
-
15044340522
-
-
note
-
For spectroscopic and analytical data of the non-deuterated compound see ref.[3a]
-
-
-
-
59
-
-
15044364054
-
-
note
-
For spectroscopic and analytical data of the non-deuterated compound see Supporting Information in ref.[4b]
-
-
-
-
60
-
-
15044355822
-
-
note
-
For spectroscopic and analytical data of the non-deuterated compound see ref.[4c] and Supporting Information in ref.[4b]
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-
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