-
1
-
-
0001527822
-
-
1. For recent reviews about polyene macrolide antibiotics see: (a) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021-2040.
-
(1995)
Chem. Rev.
, vol.95
, pp. 2021-2040
-
-
Rychnovsky, S.D.1
-
3
-
-
0004298799
-
-
Atta-ur-Rahman, Ed.; Elsevier Science, in the press
-
2. For a recent review about natural products with polyene amide structures see: Nájera, C.; Yus, M. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science, Vol. 21 in the press.
-
Studies in Natural Products Chemistry
, vol.21
-
-
Nájera, C.1
Yus, M.2
-
4
-
-
0000606066
-
-
These dianions are alkylated at the allylic position, the resulting thioesters after LDA-promoted [2.3]-sigmatropic rearrangement to the 2-mercaptocarboxylic esters and S-methylation and oxidation to the sulfoxides followed by thermal dehydrosulfenylation afforded (2E,4E)-dienoates
-
3. These dianions are alkylated at the allylic position, the resulting thioesters after LDA-promoted [2.3]-sigmatropic rearrangement to the 2-mercaptocarboxylic esters and S-methylation and oxidation to the sulfoxides followed by thermal dehydrosulfenylation afforded (2E,4E)-dienoates: Tanaka, K.; Terauchi, M.; Kaji, A. Chem. Lett. 1981, 315-318.
-
(1981)
Chem. Lett.
, pp. 315-318
-
-
Tanaka, K.1
Terauchi, M.2
Kaji, A.3
-
7
-
-
85038530762
-
-
private communication
-
5. Bernabeu, M. C. private communication.
-
-
-
Bernabeu, M.C.1
-
8
-
-
0000156734
-
-
They have been postulated as intermediates
-
6. They have been postulated as intermediates: Mandai, T.; Moriyama, T.; Tsujimoto, K.; Kawada, M.; Otera, J. Tetrahedron Lett. 1986, 27, 603-606.
-
(1986)
Tetrahedron Lett.
, vol.27
, pp. 603-606
-
-
Mandai, T.1
Moriyama, T.2
Tsujimoto, K.3
Kawada, M.4
Otera, J.5
-
9
-
-
0342275178
-
-
and references cited therein
-
7. For recent studies about lithiated vinyl sulfones see: Caturla, F.; Nájera, C. Tetrahedron 1997, 53, 11449-11464 and references cited therein.
-
(1997)
Tetrahedron
, vol.53
, pp. 11449-11464
-
-
Caturla, F.1
Nájera, C.2
-
11
-
-
37049087545
-
-
9. This is an appropriate methodology for the stereoselective introduction of the arylsulfonyl group at the terminal position of olefins: (a) Nájera, C.; Baldó, B.; Yus, M. J. Chem. Soc., Perkin Trans. 1 1988, 1029-1032.
-
(1988)
J. Chem. Soc., Perkin Trans. 1
, pp. 1029-1032
-
-
Nájera, C.1
Baldó, B.2
Yus, M.3
-
13
-
-
1842375056
-
-
(c) Grigg, R.; Nájera, C.; Sansano, J. M.; Yus, M. Synth. Commun. 1997, 27, 1111-1114.
-
(1997)
Synth. Commun.
, vol.27
, pp. 1111-1114
-
-
Grigg, R.1
Nájera, C.2
Sansano, J.M.3
Yus, M.4
-
14
-
-
33744586503
-
-
10. Miyashita, M.; Yoshihoshi, A.; Grieco, P. A. J. Org. Chem. 1977, 42, 3772-3774.
-
(1977)
J. Org. Chem.
, vol.42
, pp. 3772-3774
-
-
Miyashita, M.1
Yoshihoshi, A.2
Grieco, P.A.3
-
15
-
-
85038532741
-
-
1H NMR (300 MHz)
-
1H NMR (300 MHz)
-
-
-
-
16
-
-
85038537875
-
-
The deuterium incorporation was determined by mass spectrometry
-
12. The deuterium incorporation was determined by mass spectrometry.
-
-
-
-
17
-
-
84990149267
-
-
13. The obtention of dideuterated lactam 26 is not a proof of the existence of dilithiated lactam 25. We have proposed the possible participation of this intermediate on the basis that monolithiated lactam 23 did not react with carbonyl compounds to give compounds 15. With respect to the structure, in the solid state the lithium is on the oxygen in lithiosulfones according to the X-ray analysis: (a) Hollstein, W.; Harms, K.; Marsch, M.; Boche, G. Angew. Chem. Int. Ed. Engl. 1988, 27, 846-849.
-
(1988)
Angew. Chem. Int. Ed. Engl.
, vol.27
, pp. 846-849
-
-
Hollstein, W.1
Harms, K.2
Marsch, M.3
Boche, G.4
-
18
-
-
0025342805
-
-
(b) Gais, H-J.; Hellmann, G.; Lindner, H. J. Angew. Chem. Int. Ed. Engl. 1990, 29, 100-103.
-
(1990)
Angew. Chem. Int. Ed. Engl.
, vol.29
, pp. 100-103
-
-
Gais, H.-J.1
Hellmann, G.2
Lindner, H.J.3
-
19
-
-
0000084040
-
-
14. For reviews about β-amido and β-oxido organolithium compounds see: (a) Nájera, C.; Yus, M. Trends Org. Chem. 1991, 2, 155-181.
-
(1991)
Trends Org. Chem.
, vol.2
, pp. 155-181
-
-
Nájera, C.1
Yus, M.2
-
21
-
-
85038534530
-
-
threo = 2.5 Hz. (equation presented)
-
threo = 2.5 Hz. (equation presented)
-
-
-
-
22
-
-
0030978514
-
-
16. Lithiated β-aminoalkyl sulfones gave also stereoselective dimerization to the meso diastereomers: Alonso, D. A.; Costa, A.; Mancheño, B.; Nájera, C. Tetrahedron 1997, 53, 4791-4814.
-
(1997)
Tetrahedron
, vol.53
, pp. 4791-4814
-
-
Alonso, D.A.1
Costa, A.2
Mancheño, B.3
Nájera, C.4
-
23
-
-
85038533247
-
-
threo = 2.0 Hz
-
threo = 2.0 Hz.
-
-
-
-
25
-
-
0027751768
-
-
19. Related 6-hydroxydienoates have been used as precursors of the polyhydroxy indolizidine alkaloid castanospermine by means of successive Sharpless epoxidation-dihydroxylation reactions of the two double carbon-carbon bonds: Kim, N. S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096-7099.
-
(1993)
J. Org. Chem.
, vol.58
, pp. 7096-7099
-
-
Kim, N.S.1
Choi, J.-R.2
Cha, J.K.3
-
27
-
-
12644312578
-
-
21. Mancuso, A. J.; Huang, S.-L.; Swern, D. J. Org. Chem. 1978, 43, 2480-2482.
-
(1978)
J. Org. Chem.
, vol.43
, pp. 2480-2482
-
-
Mancuso, A.J.1
Huang, S.-L.2
Swern, D.3
-
28
-
-
0000274562
-
-
22. Axelrod, E. H.; Milne, G. M.; van Tamelen, E. E. J. Am. Chem. Soc. 1970, 92, 2139-2141.
-
(1970)
J. Am. Chem. Soc.
, vol.92
, pp. 2139-2141
-
-
Axelrod, E.H.1
Milne, G.M.2
Van Tamelen, E.E.3
-
29
-
-
85038535992
-
-
Only one diastereomer
-
23. Only one diastereomer.
-
-
-
-
30
-
-
85038533049
-
-
Mixture of diastereomers
-
24. Mixture of diastereomers.
-
-
-
-
31
-
-
85038536192
-
-
+ signal
-
+ signal.
-
-
-
|