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33847550816
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The mode of action involves blocking the S phase of the cell cycle see ref 2.
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The mode of action involves blocking the S phase of the cell cycle see ref 2.
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Rapamycin and 27-demethoxyrapamycin total syntheses: Smith, A. B., Ill; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997,119,947.
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33847552787
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Complete crystallographic data for 12, 13, 15, 49, 89, and 1 have been deposited in the Cambridge Crystallographic Data Centre.
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Complete crystallographic data for 12, 13, 15, 49, 89, and 1 have been deposited in the Cambridge Crystallographic Data Centre.
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33847560817
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Alcohol 17 could also be converted to iodide A in 94% overall yield via tosylation (TsCl, pyridine) followed by displacement with sodium iodide in DMF.
-
Alcohol 17 could also be converted to iodide A in 94% overall yield via tosylation (TsCl, pyridine) followed by displacement with sodium iodide in DMF.
-
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61
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33847571572
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We also explored the use of the norephedrine-derived oxazolidinone 11 employed in the synthesis of CP. Unfortunately the corresponding aldol product was obtained as an oil. In addition, reductive removal of the auxiliary resulted in competitive opening of the oxazolidinone ring; thus, oxazolidinone 9 was the auxiliary of choice for the construction of fragment A.
-
We also explored the use of the norephedrine-derived oxazolidinone 11 employed in the synthesis of CP. Unfortunately the corresponding aldol product was obtained as an oil. In addition, reductive removal of the auxiliary resulted in competitive opening of the oxazolidinone ring; thus, oxazolidinone 9 was the auxiliary of choice for the construction of fragment A.
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See ref 32, Chapter 11.
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See ref 32, Chapter 11.
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77
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33847567900
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Selected NOE values (%) and 'H NMR coupling constants for 36 and 39. We thank Dr. Peter Dormer for technical assistance. matrix equation presented
-
Selected NOE values (%) and 'H NMR coupling constants for 36 and 39. We thank Dr. Peter Dormer for technical assistance. matrix equation presented
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-
-
While attempting to optimize the formation of 46 via the Zhao protocol, we observed significant formation of methyl ketone and epoxide byproducts. These results suggest that formation of an epoxyphosphonium salt is competitive with Wittig olefination. A detailed discussion of the Zhao chemistry has been published and will not be repeated here; see: Arimoto, H.; Kaufman, M. D.; Kobayashi, K.; Qui, Y.; Smith, A. B., III. Synlett 1998, 765.
-
(1998)
Synlett
, pp. 765
-
-
Arimoto, H.1
Kaufman, M.D.2
Kobayashi, K.3
Qui, Y.4
Smith, A.B.5
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84
-
-
33847556361
-
-
In the Marshall synthesis of 1, a Suzuki coupling strategy was employed requiring 2 equiv of the alkyl iodide; see ref lid.
-
In the Marshall synthesis of 1, a Suzuki coupling strategy was employed requiring 2 equiv of the alkyl iodide; see ref lid.
-
-
-
-
85
-
-
33947483522
-
-
(a) Johnson, W. S.; Bailey, D. M.; Owyang, R.; Bell, R. A.; Jaques, B.; Crandall, J. K. J. Am. Chem. Soc. 1964, 56, 1959.
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(1964)
J. Am. Chem. Soc.
, vol.56
, pp. 1959
-
-
Johnson, W.S.1
Bailey, D.M.2
Owyang, R.3
Bell, R.A.4
Jaques, B.5
Crandall, J.K.6
-
87
-
-
0021062284
-
-
(a) Corey, E. J.; Pyne, S. G.; Su, W.-G. Tetrahedron Lett. 1983, 24, 4883.
-
(1983)
Tetrahedron Lett.
, vol.24
, pp. 4883
-
-
Corey, E.J.1
Pyne, S.G.2
Su, W.-G.3
-
89
-
-
33847566530
-
-
note
-
rel = 0-5.48 kJ/mol) were judged suitably disposed to facilitate displacement of the iodide by the olefin. Of these conformers, the average distance between C(I) and C(5) was only 3.05 Å (SD = 0.02 Å) while the average I-C(1)-C(5) angle was 161.2° (SD = 0.4°).
-
-
-
-
91
-
-
0000345933
-
-
For reviews on the use of high pressure in organic synthesis, see: (a) Organic Synthesis at High Pressure; Matsumoto, K., Morrin Acheson, R., Eds.; John Wiley: New York, 1991.
-
Dauben, W. G.; Gerdes, J. M.; Bunce, R. A. J. Org. Chem. 1984, 49,4293. For reviews on the use of high pressure in organic synthesis, see: (a) Organic Synthesis at High Pressure; Matsumoto, K., Morrin Acheson, R., Eds.; John Wiley: New York, 1991.
-
(1984)
J. Org. Chem.
, vol.49
, pp. 4293
-
-
Dauben, W.G.1
Gerdes, J.M.2
Bunce, R.A.3
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94
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-
0002487780
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-
Takano, S.; Akiyama, M.; Sato, S.; Ogasawara, K. Chem. Lett. 1983, 1593.
-
(1983)
Chem. Lett.
, pp. 1593
-
-
Takano, S.1
Akiyama, M.2
Sato, S.3
Ogasawara, K.4
-
95
-
-
0000710912
-
-
Ikeda, Y.; Ukai, J.; Ikeda, N.; Yamamoto, H. Tetrahedron 1987, 43, 723.
-
(1987)
Tetrahedron
, vol.43
, pp. 723
-
-
Ikeda, Y.1
Ukai, J.2
Ikeda, N.3
Yamamoto, H.4
-
96
-
-
33847539437
-
-
Heathcock has also utilized the Yamamoto protocol; see ref lOb.
-
Heathcock has also utilized the Yamamoto protocol; see ref lOb.
-
-
-
-
99
-
-
33847552575
-
-
note
-
We thank Professor Schreiber (Harvard University) for providing a sample of synthetic (-)-discodermolide.
-
-
-
-
100
-
-
33847546439
-
-
Helmchen, G., Hoffman, R. W., Mulzer, J., Schaumann, Eds.; Thieme Verlag: New York, Vol. E21b, Chapter
-
For a general discussion of nucleophilic additions to α-chiral carbonyl compounds, see: Devant, R. M.; Radunz, H.-E. In Methods of Organic Chemistry; Helmchen, G., Hoffman, R. W., Mulzer, J., Schaumann, Eds.; Thieme Verlag: New York, 1995; Vol. E21b, Chapter 1.3.
-
(1995)
Methods of Organic Chemistry
, pp. 13
-
-
Devant, R.M.1
Radunz, H.-E.2
-
101
-
-
33847561040
-
-
Paterson reported the synthesis of the enantiomer of 71; see ref 10a. However, use as a substrate for Wittig olefination was not reported.
-
Paterson reported the synthesis of the enantiomer of 71; see ref 10a. However, use as a substrate for Wittig olefination was not reported.
-
-
-
-
103
-
-
33847541976
-
-
2,3 = 9.8 Hz.
-
2,3 = 9.8 Hz.
-
-
-
-
104
-
-
33847547356
-
-
The BPS ether aldehyde 79, a substrate lacking the Weinreb amide moiety furnished the Felkin addition product 80 over the anti-Felkin adduct 81 (3:1): matrix equation presented
-
The BPS ether aldehyde 79, a substrate lacking the Weinreb amide moiety furnished the Felkin addition product 80 over the anti-Felkin adduct 81 (3:1): matrix equation presented
-
-
-
-
105
-
-
0001091444
-
-
For a discussion of chelation-controlled carbonyl additions see: Reetz, M. T. Ace. Chem. Res. 1993, 26, 462.
-
(1993)
Ace. Chem. Res.
, vol.26
, pp. 462
-
-
Reetz, M.T.1
-
106
-
-
0342371555
-
-
13C NMR data strongly supports coordination of Sn(IV) with the carbonyls of 82. (a) Santelli-Rouvier, C. Tetrahedron Lett. 1984, 25, 4371.
-
(1984)
Tetrahedron Lett.
, vol.25
, pp. 4371
-
-
Santelli-Rouvier, C.1
-
107
-
-
0000416437
-
-
(b) Yamamoto, Y.; Yatagai, H.; Ishihara, Y.; Maeda, N.; Maruyama, K. Tetrahedron 1984, 40, 2239.
-
(1984)
Tetrahedron
, vol.40
, pp. 2239
-
-
Yamamoto, Y.1
Yatagai, H.2
Ishihara, Y.3
Maeda, N.4
Maruyama, K.5
-
108
-
-
0010430624
-
-
matrix equation presented
-
Yamamoto, Y.; Nemoto, H.; Kikuchi, R.; Komatsu, H.; Suzuki, I. J. Am. Chem. Soc. 1990, 112, 8598. matrix equation presented
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 8598
-
-
Yamamoto, Y.1
Nemoto, H.2
Kikuchi, R.3
Komatsu, H.4
Suzuki, I.5
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109
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4444276636
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Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
-
(1994)
Chem. Rev.
, vol.94
, pp. 2483
-
-
Kolb, H.C.1
Vannieuwenhze, M.S.2
Sharpless, K.B.3
-
110
-
-
33847565710
-
-
note
-
3H again afforded only a 3: 1 mixture of diols. matrix equation presented
-
-
-
-
111
-
-
33847569342
-
-
Minor amounts of elimination products 91 and 92 were also observed. matrix equation presented
-
Minor amounts of elimination products 91 and 92 were also observed. matrix equation presented
-
-
-
-
112
-
-
33847568519
-
-
note
-
Both Myles and Paterson employed a two-step diene synthesis in their syntheses of discodermolide. In our hands this route did successfully deliver discodermolide in 31 total steps (22 in the longest linear sequence); however, due to the capricious yields observed, this approach was not conducive to large-scale synthesis.
-
-
-
-
113
-
-
33847569808
-
-
All attempts to remove selectively the primary PMB ether in the presence of the secondary PMB ether proved unsuccessful.
-
All attempts to remove selectively the primary PMB ether in the presence of the secondary PMB ether proved unsuccessful.
-
-
-
-
115
-
-
0009393338
-
-
Boeckman, R. K, Jr.; Potenza, J. C.; Tetrahedron Lett. 1985, 26, 11, 1411.
-
(1985)
Tetrahedron Lett.
, vol.26
, pp. 1411
-
-
Boeckman, R.K.1
Potenza, J.C.2
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116
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33847559382
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-
For a discussion on this side reaction see: Schnell, A.; Tebby, J. C. J. Chem. Soc., Perkin Trans, 11977, 1883.
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(1197)
J. Chem. Soc., Perkin Trans
, vol.7
, pp. 1883
-
-
Schnell, A.1
Tebby, J.C.2
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117
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33847563950
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-
We thank Novartis for informing us that discodermolide is stable in acetonitrile.
-
We thank Novartis for informing us that discodermolide is stable in acetonitrile.
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-
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