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1
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For a review see Ritchie, E.; Taylor, W. C. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1967; Vol. 9, p 529.
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Ritchie, E.1
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5
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8544269116
-
-
note
-
9 It belongs to the Magnoliales order and thus is somewhat related to magnolias. We thank Professor Frank R. Stermitz of Colorado State University for bringing this error to our attention.
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6
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0026705635
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Kozikowski, A.; Fauq, A. H.; Miller, J. H.; McKinney, M. Bioorg. Med. Chem. Lett. 1992, 2, 797. Malaska, M. J.; Fauq, A. H.; Kozikowski, A. P.; Aagaard, P. J.; McKinney, M. Bioorg. Med. Chem. Lett. 1993, 3, 1247. Malaska, M. J.; Fauq, A. H.; Kozikowski, A. P.; Aagaard, P. J.; McKinney, M. Bioorg. Med. Chem. Lett. 1995, 5, 61.
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0027190337
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Kozikowski, A.; Fauq, A. H.; Miller, J. H.; McKinney, M. Bioorg. Med. Chem. Lett. 1992, 2, 797. Malaska, M. J.; Fauq, A. H.; Kozikowski, A. P.; Aagaard, P. J.; McKinney, M. Bioorg. Med. Chem. Lett. 1993, 3, 1247. Malaska, M. J.; Fauq, A. H.; Kozikowski, A. P.; Aagaard, P. J.; McKinney, M. Bioorg. Med. Chem. Lett. 1995, 5, 61.
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8
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Kozikowski, A.; Fauq, A. H.; Miller, J. H.; McKinney, M. Bioorg. Med. Chem. Lett. 1992, 2, 797. Malaska, M. J.; Fauq, A. H.; Kozikowski, A. P.; Aagaard, P. J.; McKinney, M. Bioorg. Med. Chem. Lett. 1993, 3, 1247. Malaska, M. J.; Fauq, A. H.; Kozikowski, A. P.; Aagaard, P. J.; McKinney, M. Bioorg. Med. Chem. Lett. 1995, 5, 61.
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Malaska, M.J.1
Fauq, A.H.2
Kozikowski, A.P.3
Aagaard, P.J.4
McKinney, M.5
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9
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0026492964
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Miller, J. H.; Aagaard, P. J.; Gibson, V. A.; McKinney, M. J. Pharmacol. Exp. Ther. 1992, 263, 663.
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Miller, J.H.1
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Gibson, V.A.3
McKinney, M.4
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10
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0029084209
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For a communication, see: Hart, D. J.; Wu, W.-L.; Kozikowski, A. P. J. Am. Chem. Soc. 1995, 117, 9369.
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Hart, D.J.1
Wu, W.-L.2
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11
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0029096238
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-
For approaches that are very similar to ours, see: De Baecke, G.; De Clercq, P. J. Tetrahedron Lett. 1995, 36, 7515. Baldwin, J. E.; Chesworth, R.; Parker, J. S.; Russell, A. T. Tetrahedron Lett. 1995, 36, 9551. For another total synthesis and a different approach, see: Chackalamannil, S.; Davies, R. J.; Asberom, T.; Doller, D.; Leone, D. J. Am. Chem. Soc. 1996, 118, 9812.
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(1995)
Tetrahedron Lett.
, vol.36
, pp. 7515
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De Baecke, G.1
De Clercq, P.J.2
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12
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0029566963
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-
For approaches that are very similar to ours, see: De Baecke, G.; De Clercq, P. J. Tetrahedron Lett. 1995, 36, 7515. Baldwin, J. E.; Chesworth, R.; Parker, J. S.; Russell, A. T. Tetrahedron Lett. 1995, 36, 9551. For another total synthesis and a different approach, see: Chackalamannil, S.; Davies, R. J.; Asberom, T.; Doller, D.; Leone, D. J. Am. Chem. Soc. 1996, 118, 9812.
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(1995)
Tetrahedron Lett.
, vol.36
, pp. 9551
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Baldwin, J.E.1
Chesworth, R.2
Parker, J.S.3
Russell, A.T.4
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13
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0029860641
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-
For approaches that are very similar to ours, see: De Baecke, G.; De Clercq, P. J. Tetrahedron Lett. 1995, 36, 7515. Baldwin, J. E.; Chesworth, R.; Parker, J. S.; Russell, A. T. Tetrahedron Lett. 1995, 36, 9551. For another total synthesis and a different approach, see: Chackalamannil, S.; Davies, R. J.; Asberom, T.; Doller, D.; Leone, D. J. Am. Chem. Soc. 1996, 118, 9812.
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(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 9812
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Chackalamannil, S.1
Davies, R.J.2
Asberom, T.3
Doller, D.4
Leone, D.5
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14
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33746873936
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Schreiber, S. L.; Claus, R. E.; Reagan, J. Tetrahedron Lett. 1982, 23, 3867.
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Schreiber, S.L.1
Claus, R.E.2
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15
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0024463710
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Ito, Y.; Kobayashi, Y.; Kawabata, T.; Takase, M.; Terashima, S. Tetrahedron 1989, 45, 5767.
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Ito, Y.1
Kobayashi, Y.2
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Takase, M.4
Terashima, S.5
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16
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0002061964
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Hermann, J.L.1
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17
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0001229094
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Kende, A. S.; Toder, B. H. J. Org. Chem. 1982, 47, 163. Yao, Z.-J.; Wu, Y.-L. Tetrahedron Lett. 1994, 35, 157.
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Kende, A.S.1
Toder, B.H.2
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18
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0027955585
-
-
Kende, A. S.; Toder, B. H. J. Org. Chem. 1982, 47, 163. Yao, Z.-J.; Wu, Y.-L. Tetrahedron Lett. 1994, 35, 157.
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, pp. 157
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Yao, Z.-J.1
Wu, Y.-L.2
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21
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0007653848
-
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Keck, G. E.; Boden, E. P.; Mabury, S. A. J. Org. Chem. 1985, 50, 709.
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Keck, G.E.1
Boden, E.P.2
Mabury, S.A.3
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22
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0023273841
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Huang, Y.-Z., Shi, L.; Yang, J.; Cai, Z. J. Org. Chem. 1987, 52, 3558.
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Shi, L.2
Yang, J.3
Cai, Z.4
-
25
-
-
8544282213
-
-
note
-
The appearance of a small signal at about δ 6.79 in the cycloadditions of 19a and 19b suggested that a small amount of third stereoisomer was formed in these cycloaddition reactions. This signal did not appear in the Lewis acid promoted reactions.
-
-
-
-
26
-
-
8544228859
-
-
note
-
An exhaustive list of Lewis acids was not tried, but it is notable that diethylaluminum chloride (not supported on silica gel) failed to afford cycloadducts.
-
-
-
-
27
-
-
8544283578
-
-
Wladislaw, B.; Marzorati, L.; Gruber. J. Phosphorus, Sulfur, Silicon Relat. Elem. 1991, 59, 479. Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840. Byeon, C.-H. Ph.D. Thesis, The Ohio State University, Columbus, OH, 1994.
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, vol.59
, pp. 479
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Wladislaw, B.1
Marzorati, L.2
Gruber, J.3
-
28
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-
0027200915
-
-
Wladislaw, B.; Marzorati, L.; Gruber. J. Phosphorus, Sulfur, Silicon Relat. Elem. 1991, 59, 479. Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840. Byeon, C.-H. Ph.D. Thesis, The Ohio State University, Columbus, OH, 1994.
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, vol.58
, pp. 3840
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Chen, C.-Y.1
Hart, D.J.2
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29
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8544263594
-
-
Ph.D. Thesis, The Ohio State University, Columbus, OH
-
Wladislaw, B.; Marzorati, L.; Gruber. J. Phosphorus, Sulfur, Silicon Relat. Elem. 1991, 59, 479. Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840. Byeon, C.-H. Ph.D. Thesis, The Ohio State University, Columbus, OH, 1994.
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(1994)
-
-
Byeon, C.-H.1
-
30
-
-
0027195693
-
-
Cativiela, C.; Fraile, J. M.; Garcia, J. I.; Mayoral, J. A.; Pires, E.; Royo, A. J.; Figueras, F.; de Menorval, L. C. Tetrahedron 1993, 49, 4073.
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(1993)
Tetrahedron
, vol.49
, pp. 4073
-
-
Cativiela, C.1
Fraile, J.M.2
Garcia, J.I.3
Mayoral, J.A.4
Pires, E.5
Royo, A.J.6
Figueras, F.7
De Menorval, L.C.8
-
31
-
-
0008541419
-
-
McIntosh, A. V., Jr.; Meinzer, E. M.; Levin, R. H. J. Am. Chem. Soc. 1948, 70, 2955.
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McIntosh Jr., A.V.1
Meinzer, E.M.2
Levin, R.H.3
-
32
-
-
8544269869
-
-
note
-
We thank Dr. Judith Gallucci of the Department of Chemistry Crystallography Facility for determining the crystal structures of 21, 31, and 35.
-
-
-
-
34
-
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0000766966
-
-
Shiraiwa, T.; Shinjo, K.; Kurokawa, H. Bull. Chem. Soc. Jpn. 1991, 64, 3251.
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(1991)
Bull. Chem. Soc. Jpn.
, vol.64
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Shiraiwa, T.1
Shinjo, K.2
Kurokawa, H.3
-
35
-
-
0001184046
-
-
Wiley: New York
-
Dickman, D. A.; Meyers, A. I.; Smith, G. A.; Gawley, R. E. Organic Syntheses; Wiley: New York, 1990; Collect. Vol. 7, p 530.
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(1990)
Organic Syntheses
, vol.7 COLLECTIVE VOLUME
, pp. 530
-
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Dickman, D.A.1
Meyers, A.I.2
Smith, G.A.3
Gawley, R.E.4
-
36
-
-
0001620506
-
-
Tarbell, D. S.; Yamamoto, Y.; Pope, B. M. Proc. Natl. Acad. Sci. U.S.A. 1972, 69, 730.
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(1972)
Proc. Natl. Acad. Sci. U.S.A.
, vol.69
, pp. 730
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Tarbell, D.S.1
Yamamoto, Y.2
Pope, B.M.3
-
39
-
-
4043071644
-
-
Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897.
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(1971)
J. Am. Chem. Soc.
, vol.93
, pp. 2897
-
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Borch, R.F.1
Bernstein, M.D.2
Durst, H.D.3
-
40
-
-
8544270640
-
-
note
-
3, 75 MHz) δ 22.0 (q), 26.0 (t), 26.3 (t), 31.1 (t), 31.9 (t), 33.5 (t), 39.8 (d), 41.0 (d), 42.1 (d), 46.9 (d), 48.6 (d), 76.7 (d), 116.7 (t), 139.7 (d), 178.1 (s)]. This material could have resulted from sequential carbonyl addition, alcohol acylation, a Grob fragmentation, and vinyl sulfone reduction. (Matrix Presented)
-
-
-
-
43
-
-
8544281414
-
-
unpublished results
-
The preparation of sulfone 35 followed the same general path used to prepare sulfone 30 (see Experimental Section), only (S)-2-(hydroxymethyl)pyrrolidine was used as the starting material (Jing Li, unpublished results).
-
-
-
Li, J.1
-
44
-
-
37049107688
-
-
Metalation of β-(dimethylamino)tethyl phenyl sulfone (Barlow, K. N.; Marshall, D. R; Stirling, C. J. M. J. Chem. Soc., Perkin Trans. 2 1977, 1920) with n-BuLi followed by reaction of the resulting carbanion with cyclohexanecarbaldehyde gave a 58:42 mixture of diastereomeric β-hydroxy sulfones in 91% yield.
-
(1977)
J. Chem. Soc., Perkin Trans. 2
, pp. 1920
-
-
Barlow, K.N.1
Marshall, D.R.2
Stirling, C.J.M.3
-
45
-
-
8544276339
-
-
note
-
9
-
-
-
-
46
-
-
8544224766
-
-
Griffith, W. P.; Ley, S. V.; Whitcombe, F. P.; White, A. D. J. Chem. Soc., Chem. Commun. 1987, 39.
-
(1987)
J. Chem. Soc., Chem. Commun.
, pp. 39
-
-
Griffith, W.P.1
Ley, S.V.2
Whitcombe, F.P.3
White, A.D.4
-
47
-
-
0000693748
-
-
For alternative methods for conducting this elimination which were not tried, see: Keck, G. E.; Savin, K. A.; Weglarz, M. A. J. Org. Chem. 1995, 60, 3194.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 3194
-
-
Keck, G.E.1
Savin, K.A.2
Weglarz, M.A.3
-
48
-
-
33646109252
-
-
Bowden, K.; Heilbron, I. M.; Jones, E. R. H.; Weedon, B. C. L. J. Chem. Soc. 1946, 39.
-
(1946)
J. Chem. Soc.
, pp. 39
-
-
Bowden, K.1
Heilbron, I.M.2
Jones, E.R.H.3
Weedon, B.C.L.4
-
49
-
-
8544245462
-
-
note
-
2 Spectral data were also in accord with the assigned structure.
-
-
-
-
50
-
-
8544277772
-
-
note
-
We thank Professor Viresh Rawal for kindly providing a sample of the natural product.
-
-
-
-
51
-
-
8544256807
-
-
note
-
The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
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