-
1
-
-
0030048612
-
-
E.g., FR901483: (a) Sakamoto, K.; Tsujii, E.; Abe, F.; Nakanishi, T.; Yamashita, M.; Shigematsu, N.; Izumi, S.; Okuhara M. J. Antibiot. 1996, 49, 37 (isolation). (b) Snider, B. B.; Lin, H.; Foxman, B. M. J. Am. Chem. Soc. 1999, 121, 7778 (synthesis). TAN-1251: (c) Shirafuji, H.; Tsubotani, S.; Ishimaru, T.; Harada, S. World Patent WO 91/13887 (1991) to Takeda Chemical Industries, Ltd. (isolation). (d) Nagumo, S.; Nishida, A.; Yamazaki, C.; Murashige, K.; Kawahara, N. Tetrahedron Lett. 1998, 39, 4493 (synthesis). Cyclindricines: (e) Blackman, A. J.; Li, C.; Hockless, D. C. R.; Skelton, B. H. Tetrahedron 1993, 49, 8645 (isolation). (f) Molander, G. A.; Rönn, M. J. Org. Chem. 1999, 64, 5183 (synthesis).
-
(1996)
J. Antibiot.
, vol.49
, pp. 37
-
-
Sakamoto, K.1
Tsujii, E.2
Abe, F.3
Nakanishi, T.4
Yamashita, M.5
Shigematsu, N.6
Izumi, S.7
Okuhara, M.8
-
2
-
-
0033199676
-
-
E.g., FR901483: (a) Sakamoto, K.; Tsujii, E.; Abe, F.; Nakanishi, T.; Yamashita, M.; Shigematsu, N.; Izumi, S.; Okuhara M. J. Antibiot. 1996, 49, 37 (isolation). (b) Snider, B. B.; Lin, H.; Foxman, B. M. J. Am. Chem. Soc. 1999, 121, 7778 (synthesis). TAN-1251: (c) Shirafuji, H.; Tsubotani, S.; Ishimaru, T.; Harada, S. World Patent WO 91/13887 (1991) to Takeda Chemical Industries, Ltd. (isolation). (d) Nagumo, S.; Nishida, A.; Yamazaki, C.; Murashige, K.; Kawahara, N. Tetrahedron Lett. 1998, 39, 4493 (synthesis). Cyclindricines: (e) Blackman, A. J.; Li, C.; Hockless, D. C. R.; Skelton, B. H. Tetrahedron 1993, 49, 8645 (isolation). (f) Molander, G. A.; Rönn, M. J. Org. Chem. 1999, 64, 5183 (synthesis).
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 7778
-
-
Snider, B.B.1
Lin, H.2
Foxman, B.M.3
-
3
-
-
0342892663
-
-
World Patent WO 91/13887 (1991) to Takeda Chemical Industries, Ltd. (isolation)
-
E.g., FR901483: (a) Sakamoto, K.; Tsujii, E.; Abe, F.; Nakanishi, T.; Yamashita, M.; Shigematsu, N.; Izumi, S.; Okuhara M. J. Antibiot. 1996, 49, 37 (isolation). (b) Snider, B. B.; Lin, H.; Foxman, B. M. J. Am. Chem. Soc. 1999, 121, 7778 (synthesis). TAN-1251: (c) Shirafuji, H.; Tsubotani, S.; Ishimaru, T.; Harada, S. World Patent WO 91/13887 (1991) to Takeda Chemical Industries, Ltd. (isolation). (d) Nagumo, S.; Nishida, A.; Yamazaki, C.; Murashige, K.; Kawahara, N. Tetrahedron Lett. 1998, 39, 4493 (synthesis). Cyclindricines: (e) Blackman, A. J.; Li, C.; Hockless, D. C. R.; Skelton, B. H. Tetrahedron 1993, 49, 8645 (isolation). (f) Molander, G. A.; Rönn, M. J. Org. Chem. 1999, 64, 5183 (synthesis).
-
-
-
Shirafuji, H.1
Tsubotani, S.2
Ishimaru, T.3
Harada, S.4
-
4
-
-
0032543489
-
-
E.g., FR901483: (a) Sakamoto, K.; Tsujii, E.; Abe, F.; Nakanishi, T.; Yamashita, M.; Shigematsu, N.; Izumi, S.; Okuhara M. J. Antibiot. 1996, 49, 37 (isolation). (b) Snider, B. B.; Lin, H.; Foxman, B. M. J. Am. Chem. Soc. 1999, 121, 7778 (synthesis). TAN-1251: (c) Shirafuji, H.; Tsubotani, S.; Ishimaru, T.; Harada, S. World Patent WO 91/13887 (1991) to Takeda Chemical Industries, Ltd. (isolation). (d) Nagumo, S.; Nishida, A.; Yamazaki, C.; Murashige, K.; Kawahara, N. Tetrahedron Lett. 1998, 39, 4493 (synthesis). Cyclindricines: (e) Blackman, A. J.; Li, C.; Hockless, D. C. R.; Skelton, B. H. Tetrahedron 1993, 49, 8645 (isolation). (f) Molander, G. A.; Rönn, M. J. Org. Chem. 1999, 64, 5183 (synthesis).
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 4493
-
-
Nagumo, S.1
Nishida, A.2
Yamazaki, C.3
Murashige, K.4
Kawahara, N.5
-
5
-
-
0027301895
-
-
E.g., FR901483: (a) Sakamoto, K.; Tsujii, E.; Abe, F.; Nakanishi, T.; Yamashita, M.; Shigematsu, N.; Izumi, S.; Okuhara M. J. Antibiot. 1996, 49, 37 (isolation). (b) Snider, B. B.; Lin, H.; Foxman, B. M. J. Am. Chem. Soc. 1999, 121, 7778 (synthesis). TAN-1251: (c) Shirafuji, H.; Tsubotani, S.; Ishimaru, T.; Harada, S. World Patent WO 91/13887 (1991) to Takeda Chemical Industries, Ltd. (isolation). (d) Nagumo, S.; Nishida, A.; Yamazaki, C.; Murashige, K.; Kawahara, N. Tetrahedron Lett. 1998, 39, 4493 (synthesis). Cyclindricines: (e) Blackman, A. J.; Li, C.; Hockless, D. C. R.; Skelton, B. H. Tetrahedron 1993, 49, 8645 (isolation). (f) Molander, G. A.; Rönn, M. J. Org. Chem. 1999, 64, 5183 (synthesis).
-
(1993)
Tetrahedron
, vol.49
, pp. 8645
-
-
Blackman, A.J.1
Li, C.2
Hockless, D.C.R.3
Skelton, B.H.4
-
6
-
-
0344436088
-
-
E.g., FR901483: (a) Sakamoto, K.; Tsujii, E.; Abe, F.; Nakanishi, T.; Yamashita, M.; Shigematsu, N.; Izumi, S.; Okuhara M. J. Antibiot. 1996, 49, 37 (isolation). (b) Snider, B. B.; Lin, H.; Foxman, B. M. J. Am. Chem. Soc. 1999, 121, 7778 (synthesis). TAN-1251: (c) Shirafuji, H.; Tsubotani, S.; Ishimaru, T.; Harada, S. World Patent WO 91/13887 (1991) to Takeda Chemical Industries, Ltd. (isolation). (d) Nagumo, S.; Nishida, A.; Yamazaki, C.; Murashige, K.; Kawahara, N. Tetrahedron Lett. 1998, 39, 4493 (synthesis). Cyclindricines: (e) Blackman, A. J.; Li, C.; Hockless, D. C. R.; Skelton, B. H. Tetrahedron 1993, 49, 8645 (isolation). (f) Molander, G. A.; Rönn, M. J. Org. Chem. 1999, 64, 5183 (synthesis).
-
(1999)
J. Org. Chem.
, vol.64
, pp. 5183
-
-
Molander, G.A.1
Rönn, M.2
-
7
-
-
0000565676
-
-
Tamura, Y.; Yakura, T.; Haruta, J.-I.; Kita, Y. J. Org. Chem. 1987, 52, 2, 3927.
-
(1987)
J. Org. Chem.
, vol.52
, Issue.2
, pp. 3927
-
-
Tamura, Y.1
Yakura, T.2
Haruta, J.-I.3
Kita, Y.4
-
8
-
-
0342458391
-
-
Pearson, W. H., Ed.; JAI Press: Greenwich, CT
-
(a) Knapp S. In Advances in Heterocyclic Natural Product Synthesis; Pearson, W. H., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 3, p 57. It is well recognized that imidates react preferentially at nitrogen with a variety of electrophiles; cf.:
-
(1996)
Advances in Heterocyclic Natural Product Synthesis
, vol.3
, pp. 57
-
-
Knapp, S.1
-
9
-
-
0001311980
-
-
Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, UK, Chapter 8, see esp. pp 490 ff.
-
(b) Tennant, G. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, UK, 1979; Vol. 2, Chapter 8, pp 385-590, see esp. pp 490 ff.
-
(1979)
Comprehensive Organic Chemistry
, vol.2
, pp. 385-590
-
-
Tennant, G.1
-
10
-
-
0000655751
-
-
Trost, B. M., Ed.; Pergamnon Press: Oxford, UK, Chapter 2.7, see esp. pp 529 ff. and references cited in b-c
-
(c) Kantlehner, W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamnon Press: Oxford, UK, 1991; Vol. 6, Chapter 2.7, pp 485-599, see esp. pp 529 ff. and references cited in b-c.
-
(1991)
Comprehensive Organic Synthesis
, vol.6
, pp. 485-599
-
-
Kantlehner, W.1
-
11
-
-
0032566026
-
-
Braun, N. A.; Ciufolini, M. A.; Peters, K.; Peters, E.-M. Tetrahedron Lett. 1998, 39, 4667.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 4667
-
-
Braun, N.A.1
Ciufolini, M.A.2
Peters, K.3
Peters, E.-M.4
-
12
-
-
0033516707
-
-
Braun, N. A.; Bray, J.; Ciufolini, M. A. Tetrahedron Lett. 1999, 40, 4985.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 4985
-
-
Braun, N.A.1
Bray, J.2
Ciufolini, M.A.3
-
13
-
-
2142708365
-
-
Alternative methods for the preparation of related spiroheterocycles: (a) Bryce, M. R.; Gardiner, J. M.; Horton, P. J.; Smith, S. A. J. Chem. Res., Synop. 1989, 1. (b) Boivin, J.; Yousfi, M.; Zard, S. Z. Tetrahedron Lett. 1997, 38, 5985. (c) Cossy, J.; Bouzide, A. Tetrahedron 1997, 53, 5775.
-
(1989)
J. Chem. Res., Synop.
, pp. 1
-
-
Bryce, M.R.1
Gardiner, J.M.2
Horton, P.J.3
Smith, S.A.4
-
14
-
-
0030738042
-
-
Alternative methods for the preparation of related spiroheterocycles: (a) Bryce, M. R.; Gardiner, J. M.; Horton, P. J.; Smith, S. A. J. Chem. Res., Synop. 1989, 1. (b) Boivin, J.; Yousfi, M.; Zard, S. Z. Tetrahedron Lett. 1997, 38, 5985. (c) Cossy, J.; Bouzide, A. Tetrahedron 1997, 53, 5775.
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 5985
-
-
Boivin, J.1
Yousfi, M.2
Zard, S.Z.3
-
15
-
-
0030896543
-
-
Alternative methods for the preparation of related spiroheterocycles: (a) Bryce, M. R.; Gardiner, J. M.; Horton, P. J.; Smith, S. A. J. Chem. Res., Synop. 1989, 1. (b) Boivin, J.; Yousfi, M.; Zard, S. Z. Tetrahedron Lett. 1997, 38, 5985. (c) Cossy, J.; Bouzide, A. Tetrahedron 1997, 53, 5775.
-
(1997)
Tetrahedron
, vol.53
, pp. 5775
-
-
Cossy, J.1
Bouzide, A.2
-
17
-
-
0000179169
-
-
Kita, Y.; Tohma, H.; Kikuchi, K.; Inagaki, M.; Yakura, T. J. Org. Chem. 1991, 56, 435.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 435
-
-
Kita, Y.1
Tohma, H.2
Kikuchi, K.3
Inagaki, M.4
Yakura, T.5
-
18
-
-
22644449622
-
-
Peters, K.; Peters, E.-M.; Braun, N. A.; Ciufolini, M. A. Z. Kristallogr. NCS 1999, 214, 273.
-
(1999)
Z. Kristallogr. NCS
, vol.214
, pp. 273
-
-
Peters, K.1
Peters, E.-M.2
Braun, N.A.3
Ciufolini, M.A.4
-
19
-
-
0003084776
-
-
Kita, Y.; Egi, M.; Okajima, A.; Ohtsubo, M.; Takada, T.; Tohma, H. J. Chem. Soc., Chem. Commun. 1996, 1491.
-
(1996)
J. Chem. Soc., Chem. Commun.
, pp. 1491
-
-
Kita, Y.1
Egi, M.2
Okajima, A.3
Ohtsubo, M.4
Takada, T.5
Tohma, H.6
-
20
-
-
0343763687
-
-
note
-
It may also be surmised that adventitious moisture might have promoted hydolysis of the imino ether, resulting in liberation of MeOH. However, it is not likely that the reaction medium contained enough water to permit formation of 27-29 in the observed yields. In addition, products of hydroxylation of the substrate (cf. 25/26, Z = H) would also have resulted if sufficient moisture were present in the system, as it happens indeed when similar phenols of the type are exposed to DIB in moist trifloroethanol.
-
-
-
-
21
-
-
0343327756
-
-
note
-
All computational work described herein was carried out with the PC-based Hyperchem package, available from Hypercube, Inc., Ontario, Canada.
-
-
-
-
22
-
-
0004288526
-
-
VCH: New York, NY
-
Cf., e.g.: (a) Lambert, J. B.; Takeuchi, Y. Cyclic Organonitrogen Stereodynamics; VCH: New York, NY, 1992; pp 76 ff. (b) Tennant, G. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, UK, 1979; Vol. 2 (Sutherland, I. O., Ed.), Chapter 8, pp 385-590. See especially pp 396-7 and references therein.
-
(1992)
Cyclic Organonitrogen Stereodynamics
-
-
Lambert, J.B.1
Takeuchi, Y.2
-
23
-
-
0001311980
-
-
Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, UK, (Sutherland, I. O., Ed.), Chapter 8. See especially pp 396-7 and references therein
-
Cf., e.g.: (a) Lambert, J. B.; Takeuchi, Y. Cyclic Organonitrogen Stereodynamics; VCH: New York, NY, 1992; pp 76 ff. (b) Tennant, G. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, UK, 1979; Vol. 2 (Sutherland, I. O., Ed.), Chapter 8, pp 385-590. See especially pp 396-7 and references therein.
-
(1979)
Comprehensive Organic Chemistry
, vol.2
, pp. 385-590
-
-
Tennant, G.1
-
27
-
-
0000074104
-
-
Wiley: New York
-
(b) Burgess, E. M.; Penton, H. R., Jr.; Taylor, E. A.; Williams, W. M. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, p 788.
-
(1988)
Organic Syntheses
, vol.6 COLLECT
, pp. 788
-
-
Burgess, E.M.1
Penton H.R., Jr.2
Taylor, E.A.3
Williams, W.M.4
-
29
-
-
0028810543
-
-
(b) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1995, 117, 11106.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 11106
-
-
Wipf, P.1
Kim, Y.2
Goldstein, D.M.3
-
31
-
-
22844455931
-
-
Peters, K.; Peters, E.-M.; Braun, N. A.; Ciufolini, M. A. Z. Kristallogr. NCS 1999, 214, 555.
-
(1999)
Z. Kristallogr. NCS
, vol.214
, pp. 555
-
-
Peters, K.1
Peters, E.-M.2
Braun, N.A.3
Ciufolini, M.A.4
-
32
-
-
0000517303
-
-
Cf., e.g.: (a) Chow, Y. L.; Colón, C. J.; Tan, J. N. S. Can. J. Chem. 1968, 46, 2821. (b) Lunazzi, L.; Cerioni, G.; Foresti, E.; Macciantelli, D. J. Chem. Soc., Perkin Trans. 2 1980, 717 . See also: Johnson, F. Chem. Rev. 1968, 68, 375.
-
(1968)
Can. J. Chem.
, vol.46
, pp. 2821
-
-
Chow, Y.L.1
Colón, C.J.2
Tan, J.N.S.3
-
33
-
-
0002571384
-
-
Cf., e.g.: (a) Chow, Y. L.; Colón, C. J.; Tan, J. N. S. Can. J. Chem. 1968, 46, 2821. (b) Lunazzi, L.; Cerioni, G.; Foresti, E.; Macciantelli, D. J. Chem. Soc., Perkin Trans. 2 1980, 717 . See also: Johnson, F. Chem. Rev. 1968, 68, 375.
-
(1980)
J. Chem. Soc., Perkin Trans. 2
, pp. 717
-
-
Lunazzi, L.1
Cerioni, G.2
Foresti, E.3
Macciantelli, D.4
-
34
-
-
33748542524
-
-
Cf., e.g.: (a) Chow, Y. L.; Colón, C. J.; Tan, J. N. S. Can. J. Chem. 1968, 46, 2821. (b) Lunazzi, L.; Cerioni, G.; Foresti, E.; Macciantelli, D. J. Chem. Soc., Perkin Trans. 2 1980, 717 . See also: Johnson, F. Chem. Rev. 1968, 68, 375.
-
(1968)
Chem. Rev.
, vol.68
, pp. 375
-
-
Johnson, F.1
-
35
-
-
0343763686
-
-
note
-
(a) Calculated by molecular mechanics (MM+). This probably represent a lower limit for this value, since the MM+ force field tends to underestimate DE's for conformers of highly strained systems such as the ones discussed herein. (b) Approximate transition state structures were created by fixing the distance between the reacting atoms at 2.5 Å and by allowing the remainder of the molecular framework to relax in the MM+ force field.
-
-
-
-
36
-
-
0342892657
-
-
note
-
Implicit in this surmise was the assumption that the reversibility of the conjugate addition of the OH group to the dienone would probably lead to a thermodynamic product.
-
-
-
-
37
-
-
0343763683
-
-
note
-
Some degradation of the substrate became evident after 12 h of exposure to the Dess-Martin oxidant.
-
-
-
-
39
-
-
26344471034
-
Electrochemical Series
-
Weast, R. C., Ed.; CRC Press: Boca Raton, FL
-
Vanysek P. Electrochemical Series. In Handbook of Chemistry and Physics, 1st student version; Weast, R. C., Ed.; CRC Press: Boca Raton, FL, 1987; pp D91-D98.
-
(1987)
Handbook of Chemistry and Physics, 1st Student Version
-
-
Vanysek, P.1
-
40
-
-
0000285539
-
-
E.g.: Awang, D. V. C, Vincent, A. Can. J. Chem. 1980, 58, 1589. Moriarty, R. M.; Sultana, M. J. Am. Chem. Soc. 1985, 107, 4559.
-
(1980)
Can. J. Chem.
, vol.58
, pp. 1589
-
-
Awang, D.V.C.1
Vincent, A.2
-
41
-
-
0013601186
-
-
E.g.: Awang, D. V. C, Vincent, A. Can. J. Chem. 1980, 58, 1589. Moriarty, R. M.; Sultana, M. J. Am. Chem. Soc. 1985, 107, 4559.
-
(1985)
J. Am. Chem. Soc.
, vol.107
, pp. 4559
-
-
Moriarty, R.M.1
Sultana, M.2
-
42
-
-
0033593279
-
-
Example of an analogous process: Pihko, P. M.; Koskinen, Ari M. P.; Nissinen, M. J.; Rissanen, K. J. Org. Chem. 1999, 64, 652.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 652
-
-
Pihko, P.M.1
Koskinen, A.M.P.2
Nissinen, M.J.3
Rissanen, K.4
-
43
-
-
0025831524
-
-
For related quinonimine syntheses see ref 10 as well as: (a) Barret, R.; Daudon, M. Tetrahedron Lett. 1991, 32, 2133-2134. (b) Kita, Y.; Egi, M.; Okajima, A.; Ohtsubo, M.; Takada, T.; Tohma, H. Chem. Commun. 1996, 1491-1492. (c) Related spirocycles formally derived from indoles: Rodriguez, J. G.; Urrutia, A.; de Diego, J. E.; Martinez-Alcazar, M. P.; Fonseca, I. J. Org. Chem. 1998, 63, 4332- 4337.
-
(1991)
Tetrahedron Lett.
, vol.32
, pp. 2133-2134
-
-
Barret, R.1
Daudon, M.2
-
44
-
-
0003084776
-
-
For related quinonimine syntheses see ref 10 as well as: (a) Barret, R.; Daudon, M. Tetrahedron Lett. 1991, 32, 2133-2134. (b) Kita, Y.; Egi, M.; Okajima, A.; Ohtsubo, M.; Takada, T.; Tohma, H. Chem. Commun. 1996, 1491-1492. (c) Related spirocycles formally derived from indoles: Rodriguez, J. G.; Urrutia, A.; de Diego, J. E.; Martinez-Alcazar, M. P.; Fonseca, I. J. Org. Chem. 1998, 63, 4332- 4337.
-
(1996)
Chem. Commun.
, pp. 1491-1492
-
-
Kita, Y.1
Egi, M.2
Okajima, A.3
Ohtsubo, M.4
Takada, T.5
Tohma, H.6
-
45
-
-
1542738328
-
-
For related quinonimine syntheses see ref 10 as well as: (a) Barret, R.; Daudon, M. Tetrahedron Lett. 1991, 32, 2133-2134. (b) Kita, Y.; Egi, M.; Okajima, A.; Ohtsubo, M.; Takada, T.; Tohma, H. Chem. Commun. 1996, 1491-1492. (c) Related spirocycles formally derived from indoles: Rodriguez, J. G.; Urrutia, A.; de Diego, J. E.; Martinez-Alcazar, M. P.; Fonseca, I. J. Org. Chem. 1998, 63, 4332-4337.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 4332-4337
-
-
Rodriguez, J.G.1
Urrutia, A.2
De Diego, J.E.3
Martinez-Alcazar, M.P.4
Fonseca, I.5
-
46
-
-
0034602983
-
-
(a) Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S. Angew. Chem., Int. Ed. Engl. 2000, 39, 622, 625.
-
(2000)
Angew. Chem., Int. Ed. Engl.
, vol.39
, Issue.622
, pp. 625
-
-
Nicolaou, K.C.1
Zhong, Y.-L.2
Baran, P.S.3
-
51
-
-
0001604684
-
-
Keller, O.; Keller, W. E.; van Look, G.; Wersin, G. Org. Synth. 1984, 63, 160.
-
(1984)
Org. Synth.
, vol.63
, pp. 160
-
-
Keller, O.1
Keller, W.E.2
Van Look, G.3
Wersin, G.4
-
53
-
-
0343763681
-
-
Yi, C. S.; Martinelli, L. C.; DeWitt Blanton, C., Jr. J. Org. Chem. 1978, 43, 405.
-
(1978)
J. Org. Chem.
, vol.43
, pp. 405
-
-
Yi, C.S.1
Martinelli, L.C.2
DeWitt Blanton C., Jr.3
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