-
1
-
-
0035943269
-
-
(a) Kobayashi, J.; Hirasawa, Y.; Yoshida, N.; Morita, H. J. Org. Chem. 2001, 66, 5901.
-
(2001)
J. Org. Chem
, vol.66
, pp. 5901
-
-
Kobayashi, J.1
Hirasawa, Y.2
Yoshida, N.3
Morita, H.4
-
3
-
-
33746069670
-
-
Ishiuchi, K.; Kubota, T.; Hoshino, T.; Obara, Y.; Nakahata, N.; Kobayashi, J. Bioorg. Med. Chem. 2006, 14, 5995.
-
(2006)
Bioorg. Med. Chem
, vol.14
, pp. 5995
-
-
Ishiuchi, K.1
Kubota, T.2
Hoshino, T.3
Obara, Y.4
Nakahata, N.5
Kobayashi, J.6
-
4
-
-
25144494663
-
-
For recent reviews of Lycopodium alkaloids, see: a, Cordell, G. A, Ed, Elsevier Academic Press: New York
-
For recent reviews of Lycopodium alkaloids, see: (a) Kobayashi, J.; Morita, H. The Alkaloids: Chemistry and Biology; Cordell, G. A., Ed.; Elsevier Academic Press: New York, 2005; Vol. 61, p 1.
-
(2005)
The Alkaloids: Chemistry and Biology
, vol.61
, pp. 1
-
-
Kobayashi, J.1
Morita, H.2
-
7
-
-
77957098031
-
-
Cordell, G. A, Brossi, A, Ed, Academic Press: New York
-
(d) Ayer, W. A.; Trifonov, L. S. Alkaloids; Cordell, G. A., Brossi, A., Ed.; Academic Press: New York, 1994; Vol. 45, p 233.
-
(1994)
Alkaloids
, vol.45
, pp. 233
-
-
Ayer, W.A.1
Trifonov, L.S.2
-
9
-
-
77957072064
-
-
Brossi, A, Ed, Academic Press: New York
-
(f) MacLean, D. B. The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, p 241.
-
(1985)
The Alkaloids
, vol.26
, pp. 241
-
-
MacLean, D.B.1
-
10
-
-
53849085994
-
-
Tracey, M. R.; Hsung, R. Abstract of Papers, Presented at the 226th National Meeting of the American Chemical Society, New York, September 2003; paper ORGN-721.
-
(a) Tracey, M. R.; Hsung, R. Abstract of Papers, Presented at the 226th National Meeting of the American Chemical Society, New York, September 2003; paper ORGN-721.
-
-
-
-
13
-
-
33646443958
-
-
(d) Grant, S. W.; Zhu, K.; Zhang, Y.; Castle, S. L. Org. Lett. 2006, 8, 1867.
-
(2006)
Org. Lett
, vol.8
, pp. 1867
-
-
Grant, S.W.1
Zhu, K.2
Zhang, Y.3
Castle, S.L.4
-
15
-
-
44949188548
-
-
Bisai, A.; West, S. P.; Sarpong, R. J. Am. Chem. Soc. 2008, 130, 7222.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 7222
-
-
Bisai, A.1
West, S.P.2
Sarpong, R.3
-
16
-
-
37049074569
-
-
For application: of a one-pot procedure for α-pyridinone ring formation, see
-
For application: of a one-pot procedure for α-pyridinone ring formation, see: Kozikowski, A. P.; Reddy, E. R.; Miller, C. P. J. Chem. Soc., Perkin Trans. 1 1990, 195.
-
(1990)
J. Chem. Soc., Perkin Trans. 1
, pp. 195
-
-
Kozikowski, A.P.1
Reddy, E.R.2
Miller, C.P.3
-
20
-
-
0001512268
-
-
While 7-endo-trig conjugate additions are known, their application to the formation of a [5.4.0]undecane-2,7-dione is only precedented from Tokoroyama's studies toward the clerodane diterpenoids: Tokoroyama, T.; Tsukamoto, M.; Iio, H. Tetrahedron Lett. 1984, 25, 5067.
-
While 7-endo-trig conjugate additions are known, their application to the formation of a [5.4.0]undecane-2,7-dione is only precedented from Tokoroyama's studies toward the clerodane diterpenoids: Tokoroyama, T.; Tsukamoto, M.; Iio, H. Tetrahedron Lett. 1984, 25, 5067.
-
-
-
-
23
-
-
45549120361
-
-
(b) Alvarez, E.; Cuvigny, T.; Herve du Penhoat, C.; Julia, M. Tetrahedron 1988, 44, 119.
-
(1988)
Tetrahedron
, vol.44
, pp. 119
-
-
Alvarez, E.1
Cuvigny, T.2
Herve du Penhoat, C.3
Julia, M.4
-
26
-
-
84953502363
-
-
Levin, J. I.; Turos, E.; Weinreb, S. M. Synth. Commun. 1982, 12, 989.
-
(1982)
Synth. Commun
, vol.12
, pp. 989
-
-
Levin, J.I.1
Turos, E.2
Weinreb, S.M.3
-
27
-
-
34247133512
-
New Derivatives of Beta-Amino Acids with Anti-Thrombotic Activity
-
Eur. Patent EP 0 560 730 B1, 1996
-
Kottirsch, G.; Metternich, R.; New Derivatives of Beta-Amino Acids with Anti-Thrombotic Activity. Eur. Patent EP 0 560 730 B1, 1996.
-
-
-
Kottirsch, G.1
Metternich, R.2
-
29
-
-
33748468588
-
-
Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215.
-
(1990)
J. Am. Chem. Soc
, vol.112
, pp. 8215
-
-
Evans, D.A.1
Urpi, F.2
Somers, T.C.3
Clark, J.S.4
Bilodeau, M.T.5
-
30
-
-
0024456198
-
-
4: (a) Meyers, A. I.; Berney, D. J. Org. Chem. 1989, 54, 4673.
-
4: (a) Meyers, A. I.; Berney, D. J. Org. Chem. 1989, 54, 4673.
-
-
-
-
31
-
-
0029926182
-
-
Borane: b
-
Borane: (b) Herdeis, C.; Kaschinshki, C.; Karla, R. Tetrahedron: Asymmetry 1996, 7, 867.
-
(1996)
Tetrahedron: Asymmetry
, vol.7
, pp. 867
-
-
Herdeis, C.1
Kaschinshki, C.2
Karla, R.3
-
32
-
-
0001173496
-
-
4: (c) Umino, N.; Iwakuma, T.; Itoh, N. Tetrahedron Lett. 1976, 10, 763.
-
4: (c) Umino, N.; Iwakuma, T.; Itoh, N. Tetrahedron Lett. 1976, 10, 763.
-
-
-
-
34
-
-
0028871677
-
-
Red-A1: (e) Fréville, S.; Célérier, J. P.; Thuy, V. M.; Lhommet, G. Tetrahedron: Asymmetry 1995, 6, 2651.
-
Red-A1: (e) Fréville, S.; Célérier, J. P.; Thuy, V. M.; Lhommet, G. Tetrahedron: Asymmetry 1995, 6, 2651.
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-
-
-
35
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0030828305
-
-
3: (f) Batistini, L.; Zanardi, F.; Rassu, G.; Spanu, P.; Pelosi, G.; Fava, G. G.; Ferrari, M. B.; Casiraghi, G. Tetrahedron: Asymmetry 1997, 8, 2975.
-
3: (f) Batistini, L.; Zanardi, F.; Rassu, G.; Spanu, P.; Pelosi, G.; Fava, G. G.; Ferrari, M. B.; Casiraghi, G. Tetrahedron: Asymmetry 1997, 8, 2975.
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-
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-
36
-
-
53849101671
-
-
Masking the hydroxyl as the TBS ether did not improve amide reduction
-
Masking the hydroxyl as the TBS ether did not improve amide reduction.
-
-
-
-
37
-
-
0017892114
-
-
Thioamide formation was accomplished utilizing Lawesson's Reagent: Pedersen, B. S.; Scheibye, S.; Nilsson, N. H.; Lawesson, S. O. Bull. Soc. Chim. Belg. 1978, 87, 223.
-
Thioamide formation was accomplished utilizing Lawesson's Reagent: Pedersen, B. S.; Scheibye, S.; Nilsson, N. H.; Lawesson, S. O. Bull. Soc. Chim. Belg. 1978, 87, 223.
-
-
-
-
38
-
-
53849146192
-
-
See Supporting Information for preparation of, -26
-
See Supporting Information for preparation of (-)-26.
-
-
-
-
40
-
-
0000948339
-
-
(a) Petersen, J. S.; Tötenberg-Kaulen, S.; Rapoport, H. J. Org. Chem. 1984, 49, 2948.
-
(1984)
J. Org. Chem
, vol.49
, pp. 2948
-
-
Petersen, J.S.1
Tötenberg-Kaulen, S.2
Rapoport, H.3
-
41
-
-
0029821708
-
-
(b) Panek, J. S.; Beresis, R. T.; Celatka, C. A. J. Org. Chem. 1996, 61, 6494.
-
(1996)
J. Org. Chem
, vol.61
, pp. 6494
-
-
Panek, J.S.1
Beresis, R.T.2
Celatka, C.A.3
-
44
-
-
33947482604
-
-
Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. J. Am. Chem. Soc. 1963, 85, 207.
-
(1963)
J. Am. Chem. Soc
, vol.85
, pp. 207
-
-
Stork, G.1
Brizzolara, A.2
Landesman, H.3
Szmuszkovicz, J.4
Terrell, R.5
-
45
-
-
53849115932
-
-
Gaussian, Inc, Wallingford, CT, See Supporting Information for details regarding the described calculations
-
Frisch, M. J. Gaussian 03, revision C.01; Gaussian, Inc.: Wallingford, CT, 2004. See Supporting Information for details regarding the described calculations.
-
(2004)
Gaussian 03, revision
, Issue.C.01
-
-
Frisch, M.J.1
-
46
-
-
53849126335
-
-
Single crystal X-ray crystallographic analysis unambiguously confirmed the structural identity of compound, -42. See Supporting Information for details
-
Single crystal X-ray crystallographic analysis unambiguously confirmed the structural identity of compound (-)-42. See Supporting Information for details.
-
-
-
-
47
-
-
0001529798
-
-
13C-NMR shifts have been observed for hemiaminal salts; see: Hext, N. M.; Hansen, J.; Blake, A. J.; Hibbs, D. E.; Hursthouse, M. B.; Shishkin, O. V.; Mascal, M. J. Org. Chem. 1998, 63, 6016.
-
13C-NMR shifts have been observed for hemiaminal salts; see: Hext, N. M.; Hansen, J.; Blake, A. J.; Hibbs, D. E.; Hursthouse, M. B.; Shishkin, O. V.; Mascal, M. J. Org. Chem. 1998, 63, 6016.
-
-
-
-
48
-
-
53849139611
-
-
See Supporting Information for details
-
See Supporting Information for details.
-
-
-
-
51
-
-
53849126334
-
-
Increasing reaction time for the epimerization of (-)-42 to 46 did not effect the ratio after 18 h (1:3, respectively), suggesting that this represents the equilibrium mixture for the specified conditions.
-
Increasing reaction time for the epimerization of (-)-42 to 46 did not effect the ratio after 18 h (1:3, respectively), suggesting that this represents the equilibrium mixture for the specified conditions.
-
-
-
-
52
-
-
53849105965
-
-
2) afforded a mixture of silylated secondary hydroxyl, the epimeric C(12) protected silylated secondary hydroxyl, as well as the bissilylated secondary hydroxyl C(5) and C(12) enol ether. These reaction byproducts were minimized by employing 2,6-di-tert-butyl-4-methylpyridine (DtBMP) as a base.
-
2) afforded a mixture of silylated secondary hydroxyl, the epimeric C(12) protected silylated secondary hydroxyl, as well as the bissilylated secondary hydroxyl C(5) and C(12) enol ether. These reaction byproducts were minimized by employing 2,6-di-tert-butyl-4-methylpyridine (DtBMP) as a base.
-
-
-
-
55
-
-
0001014077
-
-
(b) Heathcock, C. H.; Ruggeri, R. B.; McClure, K. F. J. Org. Chem. 1992, 57, 2554.
-
(1992)
J. Org. Chem
, vol.57
, pp. 2554
-
-
Heathcock, C.H.1
Ruggeri, R.B.2
McClure, K.F.3
-
56
-
-
0028959987
-
-
(c) Heathcock, C. H.; Kath, J. C.; Ruggeri, R. B. J. Org. Chem. 1995, 60, 1120.
-
(1995)
J. Org. Chem
, vol.60
, pp. 1120
-
-
Heathcock, C.H.1
Kath, J.C.2
Ruggeri, R.B.3
-
57
-
-
34547434793
-
-
Diaba, F.; Ricou, E.; Bonjoch, J. Org. Lett. 2007, 9, 2633.
-
(2007)
Org. Lett
, vol.9
, pp. 2633
-
-
Diaba, F.1
Ricou, E.2
Bonjoch, J.3
-
58
-
-
0000802385
-
-
Boukherroub, R.; Chatgilialoglu, C.; Manuel, G. Organometallics 1996, 15, 1508.
-
(1996)
Organometallics
, vol.15
, pp. 1508
-
-
Boukherroub, R.1
Chatgilialoglu, C.2
Manuel, G.3
-
59
-
-
0030041404
-
-
(a) Kozikowski, A. P.; Ding, Q.; Saxena, A.; Doctor, B. P. Bioorg. Med. Chem. Lett. 1996, 6, 259.
-
(1996)
Bioorg. Med. Chem. Lett
, vol.6
, pp. 259
-
-
Kozikowski, A.P.1
Ding, Q.2
Saxena, A.3
Doctor, B.P.4
-
60
-
-
0034803791
-
-
(b) Camps, P.; Muñoz-Torrero, D.; Simon, M. Synth. Commun. 2001, 31, 3507.
-
(2001)
Synth. Commun
, vol.31
, pp. 3507
-
-
Camps, P.1
Muñoz-Torrero, D.2
Simon, M.3
-
61
-
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37049074569
-
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(c) Kozikowski, A. P.; Reddy, E. R.; Miller, C. P. J. Chem. Soc., Perkin Trans 1 1990, 195.
-
(1990)
J. Chem. Soc., Perkin Trans 1
, pp. 195
-
-
Kozikowski, A.P.1
Reddy, E.R.2
Miller, C.P.3
-
62
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0035829165
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Högenauer, K.; Baumann, K.; Enz, A.; Mulzer, J. Bioorg. Med. Chem. Lett. 2001, 11, 2627.
-
(2001)
Bioorg. Med. Chem. Lett
, vol.11
, pp. 2627
-
-
Högenauer, K.1
Baumann, K.2
Enz, A.3
Mulzer, J.4
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63
-
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0031868270
-
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Hay, L. A.; Koenig, T. M.; Ginah, F. O.; Copp, J. D.; Mitchell, D. J. Org. Chem. 1998, 63, 5050.
-
(1998)
J. Org. Chem
, vol.63
, pp. 5050
-
-
Hay, L.A.1
Koenig, T.M.2
Ginah, F.O.3
Copp, J.D.4
Mitchell, D.5
-
64
-
-
53849109363
-
-
See Supporting Information for details
-
See Supporting Information for details.
-
-
-
-
66
-
-
38749083069
-
-
Formation of compound (-)-61 can be understood as a conjugate addition of cyanide to the unsaturated amide prior to ring closure, followed by ring closure, and then oxidation, thermodynamically driven by aromatization to the α-pyridinone ring. See the following reference for a similar eliminative, aromatization event: Donohue, T. J.; Fishlock, L. P.; Procopiou, P. A. Org. Lett. 2008, 10, 285.
-
Formation of compound (-)-61 can be understood as a conjugate addition of cyanide to the unsaturated amide prior to ring closure, followed by ring closure, and then oxidation, thermodynamically driven by aromatization to the α-pyridinone ring. See the following reference for a similar eliminative, aromatization event: Donohue, T. J.; Fishlock, L. P.; Procopiou, P. A. Org. Lett. 2008, 10, 285.
-
-
-
-
68
-
-
10644266761
-
-
Conditions examined to convert 63 or 64 to (-)-lyconadin B (2) included: Resubjection to reaction conditions. Treatment with acid: (a) Kan, W. M.; Cheng, C.-L.; Chern, C.-Y Synth. Commun. 2004, 34, 4257.
-
Conditions examined to convert 63 or 64 to (-)-lyconadin B (2) included: Resubjection to reaction conditions. Treatment with acid: (a) Kan, W. M.; Cheng, C.-L.; Chern, C.-Y Synth. Commun. 2004, 34, 4257.
-
-
-
-
69
-
-
0040595025
-
-
Thermal dehydration: (b) Citterio, A.; Carnevali, E.; Farina, A.; Meille, V.; Alini, S.; Cotarca, L. Org. Prep. Proced. Int. 1997, 29, 465.
-
Thermal dehydration: (b) Citterio, A.; Carnevali, E.; Farina, A.; Meille, V.; Alini, S.; Cotarca, L. Org. Prep. Proced. Int. 1997, 29, 465.
-
-
-
-
70
-
-
33646858600
-
-
Chemical dehydration: (c) Pawlowski, M.; Maurin, J. K.; Leniewshki, A.; Wojtasiewicz, K.; Czarnocki, Z. Heterocycles 2005, 65, 9.
-
Chemical dehydration: (c) Pawlowski, M.; Maurin, J. K.; Leniewshki, A.; Wojtasiewicz, K.; Czarnocki, Z. Heterocycles 2005, 65, 9.
-
-
-
-
71
-
-
53849087677
-
-
A rationale for differences in the conditions required for optimal formation of (+)-lyconadin A (1) and (-)-lyconadin B (2) is not apparent to the authors.
-
A rationale for differences in the conditions required for optimal formation of (+)-lyconadin A (1) and (-)-lyconadin B (2) is not apparent to the authors.
-
-
-
-
72
-
-
53849125617
-
-
See Supporting Information for details
-
See Supporting Information for details.
-
-
-
-
73
-
-
33947088667
-
-
Martin sulfurane was handled and stored according to the procedures described herein: Arhart, R. J.; Martin, J. C. J. Am. Chem. Soc. 1972, 94, 5003.
-
Martin sulfurane was handled and stored according to the procedures described herein: Arhart, R. J.; Martin, J. C. J. Am. Chem. Soc. 1972, 94, 5003.
-
-
-
-
74
-
-
53849125204
-
-
Lithium di-iso-propylamide was prepared as follows: Freshly distilled di-iso-propylamine (1.4 mL, 10 mmol, 1.1 equiv) was dissolved in tetrahydrofuran (15 mL) and cooled to 0°C. n-Butyl lithium (6.6 mL, 1.37 M solution in tetrahydrofuran) was added dropwise over 5 min, and the mixture was stirred for 1 h at 0°C. The resulting lithium di-iso-propylamide solution (0.39 M) was then used immediately in the reaction.
-
Lithium di-iso-propylamide was prepared as follows: Freshly distilled di-iso-propylamine (1.4 mL, 10 mmol, 1.1 equiv) was dissolved in tetrahydrofuran (15 mL) and cooled to 0°C. n-Butyl lithium (6.6 mL, 1.37 M solution in tetrahydrofuran) was added dropwise over 5 min, and the mixture was stirred for 1 h at 0°C. The resulting lithium di-iso-propylamide solution (0.39 M) was then used immediately in the reaction.
-
-
-
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