-
1
-
-
0032761924
-
-
The term "bisorbicillinoids" was recently introduced by us to describe all dimeric natural products derived from sorbicillin: K. C. Nicolaou, R. Jautelat, G. Vassilikogiannakis, P. S. Baran, K. B. Simonsen, Chem. Eur. J. 1999, 5, 3651-3665.
-
(1999)
Chem. Eur. J.
, vol.5
, pp. 3651-3665
-
-
Nicolaou, K.C.1
Jautelat, R.2
Vassilikogiannakis, G.3
Baran, P.S.4
Simonsen, K.B.5
-
2
-
-
0000090699
-
-
N. Abe, T. Murata, A. Hirota, Biosci. Biotechnol. Biochem. 1998, 62, 661-66.
-
(1998)
Biosci. Biotechnol. Biochem.
, vol.62
, pp. 661-666
-
-
Abe, N.1
Murata, T.2
Hirota, A.3
-
3
-
-
0000553098
-
-
a) N. Abe, T. Murata, A. Hirota, Biosci. Biotechnol. Biochem. 1998, 62, 2120-2126;
-
(1998)
Biosci. Biotechnol. Biochem.
, vol.62
, pp. 2120-2126
-
-
Abe, N.1
Murata, T.2
Hirota, A.3
-
4
-
-
33748644041
-
-
b) a second fungal metabolite differing from bisorbibutenolide (2) only in its relative configuration at C9 was isolated in 1997 and named trichotetronine: O. Shirota, V. Pathak, C. F. Hossain, S. Sekita, K. Takatori, M. Satake, J. Chem. Soc. Perkin Trans. I 1997, 2961-2964.
-
(1997)
J. Chem. Soc. Perkin Trans. I
, pp. 2961-2964
-
-
Shirota, O.1
Pathak, V.2
Hossain, C.F.3
Sekita, S.4
Takatori, K.5
Satake, M.6
-
5
-
-
0000745211
-
-
a) R. Andrade, W. A. Ayer, P. P. Mehe, Can. J. Chem. 1992, 70, 2526-2535;
-
(1992)
Can. J. Chem.
, vol.70
, pp. 2526-2535
-
-
Andrade, R.1
Ayer, W.A.2
Mehe, P.P.3
-
6
-
-
15844402152
-
-
b) G. A. Warr, J. A. Veitch, A. W. Walsh, G. A. Hesler, D. M. Pirnik, J. E. Leet, P.-F. M. Lin, I. A. Medina, K. D. McBrien, S. Forenza, J. M. Clark, K. S. Lam, J. Antibiot. 1996, 49, 234-240.
-
(1996)
J. Antibiot.
, vol.49
, pp. 234-240
-
-
Warr, G.A.1
Veitch, J.A.2
Walsh, A.W.3
Hesler, G.A.4
Pirnik, D.M.5
Leet, J.E.6
Lin, P.-F.M.7
Medina, I.A.8
McBrien, K.D.9
Forenza, S.10
Clark, J.M.11
Lam, K.S.12
-
7
-
-
0000345075
-
-
a) L. S. Trifonov, H. Hilpert, P. Floersheim, A. S. Dreiding, D. M. Rast, R. Skrivanova, L. Hoesch, Tetrahedron 1986, 42, 3157-3179:
-
(1986)
Tetrahedron
, vol.42
, pp. 3157-3179
-
-
Trifonov, L.S.1
Hilpert, H.2
Floersheim, P.3
Dreiding, A.S.4
Rast, D.M.5
Skrivanova, R.6
Hoesch, L.7
-
8
-
-
0028210393
-
-
b) M. Kontani, Y. Sakagami, S. Marumo, Tetrahedron Lett. 1994, 35, 2577-2580.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 2577-2580
-
-
Kontani, M.1
Sakagami, Y.2
Marumo, S.3
-
11
-
-
84985078868
-
-
a) L. S. Trifonov, A. S. Dreiding, L. Hoesch, D. M. Rast, Helv. Chim. Acta 1981, 64, 1843-1846;
-
(1981)
Helv. Chim. Acta
, vol.64
, pp. 1843-1846
-
-
Trifonov, L.S.1
Dreiding, A.S.2
Hoesch, L.3
Rast, D.M.4
-
12
-
-
0000876674
-
-
b) L. S. Trifonov, J. H. Bieri, R. Prewo, A. S. Dreiding, L. Hoesch, D. M. Rast, Tetrahedron 1983, 39, 4243-4256.
-
(1983)
Tetrahedron
, vol.39
, pp. 4243-4256
-
-
Trifonov, L.S.1
Bieri, J.H.2
Prewo, R.3
Dreiding, A.S.4
Hoesch, L.5
Rast, D.M.6
-
13
-
-
0345628131
-
-
A previous proposal regarding the biosynthesis of bisvertinol (6) from sorbicillin postulates a different pathway, in which an initial epoxidation of sorbicillin followed by reduction and then dimerization and ketalization is believed to be involved.[7]
-
A previous proposal regarding the biosynthesis of bisvertinol (6) from sorbicillin postulates a different pathway, in which an initial epoxidation of sorbicillin followed by reduction and then dimerization and ketalization is believed to be involved.[7]
-
-
-
-
14
-
-
37049161488
-
-
W. Baker, H. F. Bondy, J. F. W. McOmie, H. R. Tunnicliff, J. Chem. Soc. 1949, 2834-2835.
-
(1949)
J. Chem. Soc.
, pp. 2834-2835
-
-
Baker, W.1
Bondy, H.F.2
McOmie, J.F.W.3
Tunnicliff, H.R.4
-
15
-
-
37049042129
-
-
J. F. W. McOmie, M. S. Tute, J. Chem. Soc. 1958, 3226-3227. This method was found to be superior on larger scale to the procedure described by the Sartori group; see F. Bigi, G. Casiraghi, G. Casnati, S. Marchesi, G. Sartori, C. Vignali, Tetrahedron 1984, 40, 4081-4084.
-
(1958)
J. Chem. Soc.
, pp. 3226-3227
-
-
McOmie, J.F.W.1
Tute, M.S.2
-
16
-
-
0000521632
-
-
J. F. W. McOmie, M. S. Tute, J. Chem. Soc. 1958, 3226-3227. This method was found to be superior on larger scale to the procedure described by the Sartori group; see F. Bigi, G. Casiraghi, G. Casnati, S. Marchesi, G. Sartori, C. Vignali, Tetrahedron 1984, 40, 4081-4084.
-
(1984)
Tetrahedron
, vol.40
, pp. 4081-4084
-
-
Bigi, F.1
Casiraghi, G.2
Casnati, G.3
Marchesi, S.4
Sartori, G.5
Vignali, C.6
-
17
-
-
0345196105
-
-
13C NMR spectra of bisorbicillinol (1) and bisorbibutenolide (2)
-
13C NMR spectra of bisorbicillinol (1) and bisorbibutenolide (2).
-
-
-
-
18
-
-
0344765632
-
-
The acetate 7a did not give any Diels-Alder product 1 when heated in benzene or in AcOH for several hours
-
The acetate 7a did not give any Diels-Alder product 1 when heated in benzene or in AcOH for several hours.
-
-
-
-
20
-
-
0016647244
-
-
b) D. H. R. Barton, P. D. Magnus, J. C. Quinney, J. Chem. Soc. Perkin Trans. I 1975, 1610-1614; see also: E. Adler, K. Holmberg, Acta. Chem. Scand. Ser. B 1974, 28, 465-472.
-
(1975)
J. Chem. Soc. Perkin Trans. I
, pp. 1610-1614
-
-
Barton, D.H.R.1
Magnus, P.D.2
Quinney, J.C.3
-
21
-
-
0000292659
-
-
b) D. H. R. Barton, P. D. Magnus, J. C. Quinney, J. Chem. Soc. Perkin Trans. I 1975, 1610-1614; see also: E. Adler, K. Holmberg, Acta. Chem. Scand. Ser. B 1974, 28, 465-472.
-
(1974)
Acta. Chem. Scand. Ser. B
, vol.28
, pp. 465-472
-
-
Adler, E.1
Holmberg, K.2
-
22
-
-
0345196104
-
-
Attempts to induce 7a to react under Lewis acid catalysis conditions were also made. Interestingly, when 7a was exposed to TBSOTf or TMSOTf, 3 was the major product formed together with small amounts of 1. TBS = tert-butyldimethylsilyl, Tf = trifluormethanesulfonyl, TMS = trimethylsilyl
-
Attempts to induce 7a to react under Lewis acid catalysis conditions were also made. Interestingly, when 7a was exposed to TBSOTf or TMSOTf, 3 was the major product formed together with small amounts of 1. TBS = tert-butyldimethylsilyl, Tf = trifluormethanesulfonyl, TMS = trimethylsilyl.
-
-
-
-
23
-
-
0345628130
-
-
Trichodimerol (4) was unavailable to us for direct comparison
-
Trichodimerol (4) was unavailable to us for direct comparison.
-
-
-
-
24
-
-
0033523823
-
-
For the first synthesis of enantiomerically pure trichodimerol by dimerization of resolved acetate 7a, see D. Barnes-Seeman, E. J. Corey, Org. Lett. 1999, 1, 1503-1504.
-
(1999)
Org. Lett.
, vol.1
, pp. 1503-1504
-
-
Barnes-Seeman, D.1
Corey, E.J.2
|