-
1
-
-
0017312767
-
-
Ireland, C.; Faulkner, D. J.; Finer, J.; Clardy, J. J. Am. Chem. Soc. 1976, 98, 4664.
-
(1976)
J. Am. Chem. Soc.
, vol.98
, pp. 4664
-
-
Ireland, C.1
Faulkner, D.J.2
Finer, J.3
Clardy, J.4
-
2
-
-
0032563996
-
-
(a) For a review: Rodriguez, A. D.; Gonzalez, E.; Ramirez, C. Tetrahedron 1998, 54, 11683.
-
(1998)
Tetrahedron
, vol.54
, pp. 11683
-
-
Rodriguez, A.D.1
Gonzalez, E.2
Ramirez, C.3
-
3
-
-
0001052491
-
-
(b) Asakawa, Y.; Lin, X.; Tori, M.; Kondo, K. Phytochemistry 1990, 29, 2597.
-
(1990)
Phytochemistry
, vol.29
, pp. 2597
-
-
Asakawa, Y.1
Lin, X.2
Tori, M.3
Kondo, K.4
-
6
-
-
0023706840
-
-
(a) Mori, K.; Iguchi, K.; Yamada, N.; Yamada, Y.; Inouye, Y. Chem. Pharm. Bull. 1988, 36, 2840.
-
(1988)
Chem. Pharm. Bull.
, vol.36
, pp. 2840
-
-
Mori, K.1
Iguchi, K.2
Yamada, N.3
Yamada, Y.4
Inouye, Y.5
-
7
-
-
0021268131
-
-
(b) Tringali, C.; Piattelli, M.; Nicolosi, G. Tetrahedron 1984, 40, 799.
-
(1984)
Tetrahedron
, vol.40
, pp. 799
-
-
Tringali, C.1
Piattelli, M.2
Nicolosi, G.3
-
8
-
-
0025892345
-
-
(a) Su, J.; Zhong, Y.; Shi, K.; Cheng, Q.; Synder, J. K.; Hu, S.; Huang, T. J. Org. Chem. 1991, 56, 2337.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 2337
-
-
Su, J.1
Zhong, Y.2
Shi, K.3
Cheng, Q.4
Synder, J.K.5
Hu, S.6
Huang, T.7
-
9
-
-
0026038893
-
-
(b) Su, J.; Zong, Y.; Zeng, L.; J. Nat. Prod. 1991, 54, 380.
-
(1991)
J. Nat. Prod.
, vol.54
, pp. 380
-
-
Su, J.1
Zong, Y.2
Zeng, L.3
-
11
-
-
0034861473
-
-
For recent isolation papers: (a) Duh, C.-Y.; Chia, M.-C.; Wang, S.-K.; Chen, H.-J.; El-Garmal, A. A. H.; Dai, C.-H. J. Nat. Prod. 2001, 64, 1028.
-
(2001)
J. Nat. Prod.
, vol.64
, pp. 1028
-
-
Duh, C.-Y.1
Chia, M.-C.2
Wang, S.-K.3
Chen, H.-J.4
El-Garmal, A.A.H.5
Dai, C.-H.6
-
12
-
-
0034735970
-
-
(b) Hinkley, S. F.; Mazzola, E. P.; Fettinger, J. C.; Lam, Y.-F.; Jarvis, B. B. Phytochemistry 2000, 55, 663.
-
(2000)
Phytochemistry
, vol.55
, pp. 663
-
-
Hinkley, S.F.1
Mazzola, E.P.2
Fettinger, J.C.3
Lam, Y.-F.4
Jarvis, B.B.5
-
13
-
-
0032802620
-
-
(c) Costantino, V.; Fattorusso, E.; Mangoni, A.; Di Rosa, M.; Ianaro, A.; Aknin, M.; Gaydou, E. M. Eur. J. Org. Chem. 1999, 1, 227.
-
(1999)
Eur. J. Org. Chem.
, vol.1
, pp. 227
-
-
Costantino, V.1
Fattorusso, E.2
Mangoni, A.3
Di Rosa, M.4
Ianaro, A.5
Aknin, M.6
Gaydou, E.M.7
-
14
-
-
0017068979
-
-
Dolatriol was the first example: Pettit, G. R.; Ode, R. H.; Herald, C. L.; Von Dreele, R. B.; Michel. C. J. Am. Chem. Soc. 1976, 98, 4677. Recently, representatives of this class, known as trichoaurantianolides and guanacastepenes, have been isolated from fungi, and display the methyl migration characterizing the neodolabellanes, as well as the 5-7-6 tricyclic skeleton of the dolastanes. Benevelli, F.; Carugo, O.; Invenizzi, A. G.; Vidari, G. Tetrahedron Lett. 1995, 36, 3035. Brady, S. F.; Bondi, S. M.; Clardy, J. J. Am. Chem. Soc. 2001, 123, 9900. For a recent report on the total synthesis of guanacastepene A: Lin, S.; Dudley, G. B.; Tan, D. S.; Danishefsky, S. J. Angew, Chem., Int. Ed. 2002, 41, 2188.
-
(1976)
J. Am. Chem. Soc.
, vol.98
, pp. 4677
-
-
Pettit, G.R.1
Ode, R.H.2
Herald, C.L.3
Von Dreele, R.B.4
Michel, C.5
-
15
-
-
0028935250
-
-
Dolatriol was the first example: Pettit, G. R.; Ode, R. H.; Herald, C. L.; Von Dreele, R. B.; Michel. C. J. Am. Chem. Soc. 1976, 98, 4677. Recently, representatives of this class, known as trichoaurantianolides and guanacastepenes, have been isolated from fungi, and display the methyl migration characterizing the neodolabellanes, as well as the 5-7-6 tricyclic skeleton of the dolastanes. Benevelli, F.; Carugo, O.; Invenizzi, A. G.; Vidari, G. Tetrahedron Lett. 1995, 36, 3035. Brady, S. F.; Bondi, S. M.; Clardy, J. J. Am. Chem. Soc. 2001, 123, 9900. For a recent report on the total synthesis of guanacastepene A: Lin, S.; Dudley, G. B.; Tan, D. S.; Danishefsky, S. J. Angew, Chem., Int. Ed. 2002, 41, 2188.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 3035
-
-
Benevelli, F.1
Carugo, O.2
Invenizzi, A.G.3
Vidari, G.4
-
16
-
-
0035840943
-
-
Dolatriol was the first example: Pettit, G. R.; Ode, R. H.; Herald, C. L.; Von Dreele, R. B.; Michel. C. J. Am. Chem. Soc. 1976, 98, 4677. Recently, representatives of this class, known as trichoaurantianolides and guanacastepenes, have been isolated from fungi, and display the methyl migration characterizing the neodolabellanes, as well as the 5-7-6 tricyclic skeleton of the dolastanes. Benevelli, F.; Carugo, O.; Invenizzi, A. G.; Vidari, G. Tetrahedron Lett. 1995, 36, 3035. Brady, S. F.; Bondi, S. M.; Clardy, J. J. Am. Chem. Soc. 2001, 123, 9900. For a recent report on the total synthesis of guanacastepene A: Lin, S.; Dudley, G. B.; Tan, D. S.; Danishefsky, S. J. Angew, Chem., Int. Ed. 2002, 41, 2188.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 9900
-
-
Brady, S.F.1
Bondi, S.M.2
Clardy, J.3
-
17
-
-
0037124683
-
-
Dolatriol was the first example: Pettit, G. R.; Ode, R. H.; Herald, C. L.; Von Dreele, R. B.; Michel. C. J. Am. Chem. Soc. 1976, 98, 4677. Recently, representatives of this class, known as trichoaurantianolides and guanacastepenes, have been isolated from fungi, and display the methyl migration characterizing the neodolabellanes, as well as the 5-7-6 tricyclic skeleton of the dolastanes. Benevelli, F.; Carugo, O.; Invenizzi, A. G.; Vidari, G. Tetrahedron Lett. 1995, 36, 3035. Brady, S. F.; Bondi, S. M.; Clardy, J. J. Am. Chem. Soc. 2001, 123, 9900. For a recent report on the total synthesis of guanacastepene A: Lin, S.; Dudley, G. B.; Tan, D. S.; Danishefsky, S. J. Angew, Chem., Int. Ed. 2002, 41, 2188.
-
(2002)
J. Angew, Chem., Int. Ed.
, vol.41
, pp. 2188
-
-
Lin, S.1
Dudley, G.B.2
Tan, D.S.3
Danishefsky, S.4
-
18
-
-
0027383656
-
-
(a) Williams, D. R.; Coleman, P. J.; Nevill, C. R.; Robinson, L. A. Tetrahedron Lett. 1993, 34, 7895.
-
(1993)
Tetrahedron Lett.
, vol.34
, pp. 7895
-
-
Williams, D.R.1
Coleman, P.J.2
Nevill, C.R.3
Robinson, L.A.4
-
22
-
-
0037062894
-
-
(b) For a recent palladium-mediated approach: Hu, T.; Corey, E. J. Org. Lett. 2002, 4, 2441.
-
(2002)
Org. Lett.
, vol.4
, pp. 2441
-
-
Hu, T.1
Corey, E.J.2
-
23
-
-
0032171337
-
-
(a) Miyaoka, H.; Isaji, Y.; Kajiwara, Y.; Kunimune, I.; Yamada, Y. Tetrahedron Lett. 1998, 39, 6503.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 6503
-
-
Miyaoka, H.1
Isaji, Y.2
Kajiwara, Y.3
Kunimune, I.4
Yamada, Y.5
-
24
-
-
0001762353
-
-
(b) See also: Kato, N.; Higo, A.; Wu, X.; Takeshita, H. Heterocycles 1997, 46, 123.
-
(1997)
Heterocycles
, vol.46
, pp. 123
-
-
Kato, N.1
Higo, A.2
Wu, X.3
Takeshita, H.4
-
25
-
-
0028217045
-
-
Mehta, G.; Karra, S. R.; Krishnamurthy, N. Tetrahedron Lett. 1994, 35, 2761.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 2761
-
-
Mehta, G.1
Karra, S.R.2
Krishnamurthy, N.3
-
28
-
-
84970601693
-
-
Bowden, B. F.; Coll, J. C.; Gulbis, J. M.; Mackay, M. F.; Willis, R. H. Aust. J. Chem. 1986, 39, 803.
-
(1986)
Aust. J. Chem.
, vol.39
, pp. 803
-
-
Bowden, B.F.1
Coll, J.C.2
Gulbis, J.M.3
Mackay, M.F.4
Willis, R.H.5
-
29
-
-
0000563136
-
-
Kobayashi, M.; Son, B.-W.; Fujiwara, T.; Kyogoku, Y.; Kitagawa, I. Tetrahedron Lett. 1984, 25, 5543.
-
(1984)
Tetrahedron Lett.
, vol.25
, pp. 5543
-
-
Kobayashi, M.1
Son, B.-W.2
Fujiwara, T.3
Kyogoku, Y.4
Kitagawa, I.5
-
30
-
-
0000475867
-
3SiCl-accelerated conjugate addition reactions of organocopper reagents
-
Taylor, R. J. K. Ed.; Oxford University Press: New York
-
3SiCl-accelerated conjugate addition reactions of organocopper reagents. In Organocopper Reagents; Taylor, R. J. K. Ed.; Oxford University Press: New York, 1994; pp 129-140.
-
(1994)
Organocopper Reagents
, pp. 129-140
-
-
Nakamura, E.1
-
32
-
-
0032541271
-
-
For a general review: Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986.
-
(1998)
J. Angew. Chem., Int. Ed.
, vol.37
, pp. 1986
-
-
Corey, E.J.1
Helal, C.2
-
34
-
-
0000054568
-
-
(b) For a related reduction of an α,α-disubstituted cyclopentanone: Denmark, S. E.; Schnute, M. E.; Marcin, L. R.; Thorarensen, A. J. Org. Chem. 1995, 60, 3205.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 3205
-
-
Denmark, S.E.1
Schnute, M.E.2
Marcin, L.R.3
Thorarensen, A.4
-
35
-
-
0242497543
-
-
(a) The optical purities were determined by Mosher ester analysis: Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2534.
-
(1969)
J. Org. Chem.
, vol.34
, pp. 2534
-
-
Dale, J.A.1
Dull, D.L.2
Mosher, H.S.3
-
36
-
-
33947085552
-
-
(b) Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1973, 95, 512.
-
(1973)
J. Org. Chem.
, vol.95
, pp. 512
-
-
Dale, J.A.1
Dull, D.L.2
Mosher, H.S.3
-
37
-
-
0242582049
-
1,3-Dicyclohexylcarbodiimide-4-dimethylaminopyridine
-
Paquette, L. A., Ed.; John Wiley and Sons: Chichester, England
-
(c) The esters were prepared using a carbodiimide coupling: Albert, J. S.; Hamilton, A. D. 1,3-Dicyclohexylcarbodiimide-4-Dimethylaminopyridine. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley and Sons: Chichester, England, 1995; Vol. 3, pp 1755-1756.
-
(1995)
Encyclopedia of Reagents for Organic Synthesis
, vol.3
, pp. 1755-1756
-
-
Albert, J.S.1
Hamilton, A.D.2
-
38
-
-
0242666003
-
-
note
-
The lactone 11 was also confirmed via the unambiguous stepwise elaboration from 9 by acetylation of the secondary alcohol, TBS ether cleavage. TPAP oxidation, deacetylation with methanolic potassium carbonate, and TPAP oxidation of the resulting lactol. Keto aldehyde (-)-6 was compared to racemic material from direct oxidative cleavage of (±)-5.
-
-
-
-
39
-
-
0041807380
-
-
(a) Griffith, W. P.; Ley, S. V.; Whitcombe, G. P.; White, A. D. J. Chem. Soc., Chem. Commun. 1987, 1625.
-
(1987)
J. Chem. Soc., Chem. Commun.
, pp. 1625
-
-
Griffith, W.P.1
Ley, S.V.2
Whitcombe, G.P.3
White, A.D.4
-
41
-
-
0001416422
-
-
(a) Barton, D. H. R.; Bashiardes, G.; Fourrey, J. L. Tetrahedron Lett. 1983, 24, 1605.
-
(1983)
Tetrahedron Lett.
, vol.24
, pp. 1605
-
-
Barton, D.H.R.1
Bashiardes, G.2
Fourrey, J.L.3
-
42
-
-
0242497542
-
-
Ph.D. Thesis, Indiana University, August
-
(b) Coleman, P. J. Ph.D. Thesis, Indiana University, August 1994.
-
(1994)
-
-
Coleman, P.J.1
-
43
-
-
0242414313
-
-
note
-
2O/-78 °C), acylation with methyl chloroformate, and hydride reduction.
-
-
-
-
45
-
-
0000291557
-
-
For preparation of the stannane: Danheiser, R. L.; Romines, K. R; Koyama, H.; Gee, S, K.; Johnson, C. R.; Medich, J. R. Org. Synth. 1993, 71, 133.
-
(1993)
Org. Synth.
, vol.71
, pp. 133
-
-
Danheiser, R.L.1
Romines, K.R.2
Koyama, H.3
Gee, S.K.4
Johnson, C.R.5
Medich, J.R.6
-
46
-
-
0242414314
-
-
(a) For previous results utilizing this unprotected stannane: Kosugi, M.; Sumiya, Y.; Ohhashi, K.; Sano, H.; Migita, T. Chemistry Lett. 1985, 997.
-
(1985)
Chemistry Lett.
, pp. 997
-
-
Kosugi, M.1
Sumiya, Y.2
Ohhashi, K.3
Sano, H.4
Migita, T.5
-
47
-
-
0033556115
-
-
(b) Yasuda, N.; Yang, C.; Wells, K. M.; Jensen, M. S.; Hughes, D. L. Tetrahedron Lett. 1999, 40, 427.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 427
-
-
Yasuda, N.1
Yang, C.2
Wells, K.M.3
Jensen, M.S.4
Hughes, D.L.5
-
48
-
-
0024800205
-
-
Cook, G. K.; Hornback, W. J.; Jordan, C. L.; McDonald, J. H., III; Monroe, J. E. J. Org. Chem. 1989, 54, 5828.
-
(1989)
J. Org. Chem.
, vol.54
, pp. 5828
-
-
Cook, G.K.1
Hornback, W.J.2
Jordan, C.L.3
McDonald J.H. III4
Monroe, J.E.5
-
49
-
-
0025996116
-
-
Smith, J. C.; Henke, S. L.; Mohler, E. M.; Morgan, L.; Rajan, N. I. Synth. Comm. 1991, 21, 1999.
-
(1991)
Synth. Comm.
, vol.21
, pp. 1999
-
-
Smith, J.C.1
Henke, S.L.2
Mohler, E.M.3
Morgan, L.4
Rajan, N.I.5
-
54
-
-
1542763298
-
-
(a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446.
-
(1995)
Acc. Chem. Res.
, vol.28
, pp. 446
-
-
Grubbs, R.H.1
Miller, S.J.2
Fu, G.C.3
-
56
-
-
0033598258
-
-
(c) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs. R. H. Org. Lett. 1999, 1, 953.
-
(1999)
Org. Lett.
, vol.1
, pp. 953
-
-
Scholl, M.1
Ding, S.2
Lee, C.W.3
Grubbs, R.H.4
-
57
-
-
0242582048
-
-
(a) Rutjes, F. P. J. T.; Kooistra, T. M.; Hiemstra, H.; Schoemaker, H. E. Synth. Lett. 1998, 192.
-
(1998)
Synth. Lett.
, pp. 192
-
-
Rutjes, F.P.J.T.1
Kooistra, T.M.2
Hiemstra, H.3
Schoemaker, H.E.4
-
58
-
-
0034598054
-
-
(b) Weatherhead, G. S.; Houser, J. H.; Ford, J. G.; Jamieson. J. Y.; Schrock, R. R.; Hoveyda, A. H. Tetrahedron Lett. 2000, 41, 9553.
-
(2000)
Tetrahedron Lett.
, vol.41
, pp. 9553
-
-
Weatherhead, G.S.1
Houser, J.H.2
Ford, J.G.3
Jamieson, J.Y.4
Schrock, R.R.5
Hoveyda, A.H.6
-
62
-
-
33845469454
-
-
Aldehyde 21 was synthesized from -ethyl lactate in three steps: Banfi, L.; Bernardi, A.; Colombo, L.; Gennari, C.; Scolastico, C. J. Org. Chem. 1984, 49, 3784.
-
(1984)
J. Org. Chem.
, vol.49
, pp. 3784
-
-
Banfi, L.1
Bernardi, A.2
Colombo, L.3
Gennari, C.4
Scolastico, C.5
-
63
-
-
33845470995
-
-
(a) Heathcock, C. H.; Kiyooka, S.; Blumenkopf, T. A. J. Org. Chem. 1984, 49, 4214.
-
(1984)
J. Org. Chem.
, vol.49
, pp. 4214
-
-
Heathcock, C.H.1
Kiyooka, S.2
Blumenkopf, T.A.3
-
72
-
-
0242666001
-
-
(b) Sugasawa, S.; Yamada, S.; Narahashi, M. J. Pharm. Soc. Jpn, 1951, 71, 1345.
-
(1951)
J. Pharm. Soc. Jpn.
, vol.71
, pp. 1345
-
-
Sugasawa, S.1
Yamada, S.2
Narahashi, M.3
-
75
-
-
0028886765
-
-
Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 5998
-
-
Keck, G.E.1
Li, X.-Y.2
Krishnamurthy, D.3
-
76
-
-
0242666002
-
-
note
-
Remaining material was identified as the Mukaiyama aldol product i which was cyclized to 26 with mild acid. Unfortunately, these additional quantities of 26 exhibited greatly reduced enantiopurity.
-
-
-
-
77
-
-
0033549737
-
-
Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2398.
-
(1999)
Angew. Chem., Int. Ed.
, vol.38
, pp. 2398
-
-
Dossetter, A.G.1
Jamison, T.F.2
Jacobsen, E.N.3
-
78
-
-
0242414311
-
-
note
-
These efforts produced 26 in 50-60% ee as determined by subsequent cleavage of the methoxymethyl ether yielding 26 (R = OH), and formation of diastereomers by Mosher esterification analysis.
-
-
-
-
79
-
-
0242497541
-
-
note
-
For many entries of Table 2, the pairs of trans-2,6-pyrans 29a and cis-29b were separated by flash silica gel chromatography. Confirmation of the structure assignment was provided by comparison with authentic 30 and the subsequent X-ray diffraction study of 34.
-
-
-
-
80
-
-
0242414312
-
-
note
-
8 benzyl ethers. Electron-donating substituents, such as the p-methoxy benzyl ether (PMB) led to a highly reactive glycal 23 and poor allylation results, whereas one or more electron-withdrawing aryl substituents (nitro, chloride, and azido substituents were examined without optimization) provided for sequentially improved yields and diastereoselectivity for 29.
-
-
-
-
81
-
-
0029129180
-
-
The reactivity of the nucleophilic olefin may also be an important factor. Trials with less reactive allyltrimethylsilane and 23 generally resulted in higher selectivity. Related studies using silyl ketene acetals report modest diastereoselectivity. See: Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron 1995, 51, 9413.
-
(1995)
Tetrahedron
, vol.51
, pp. 9413
-
-
Paterson, I.1
Smith, J.D.2
Ward, R.A.3
-
82
-
-
0003536850
-
-
Pergamon Press: New York
-
The stereochemistry of the thermodynamically more stable acetal is assumed on the basis of comparisons with closely related dihydropyran systems. See: Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: New York, 1983; pp 4-21.
-
(1983)
Stereoelectronic Effects in Organic Chemistry
, pp. 4-21
-
-
Deslongchamps, P.1
-
83
-
-
15844390521
-
-
Calculations indicate similar opportunities for synclinal and anticlinal transition states: Paddon-Row: M. N.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7162. Some examples include: Denmark, S. E.; Weber, E. J. Helv. Chim. Acta 1983, 66, 1655. Danishefsky, S. J.; DeNinno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082. Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293. Fleming, I.; Dunogues, J. Smithers, R. Org. React. 1989, 37, 57.
-
(1982)
J. Am. Chem. Soc.
, vol.104
, pp. 7162
-
-
Paddon-Row, M.N.1
Rondan, N.G.2
Houk, K.N.3
-
84
-
-
67650317827
-
-
Calculations indicate similar opportunities for synclinal and anticlinal transition states: Paddon-Row: M. N.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7162. Some examples include: Denmark, S. E.; Weber, E. J. Helv. Chim. Acta 1983, 66, 1655. Danishefsky, S. J.; DeNinno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082. Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293. Fleming, I.; Dunogues, J. Smithers, R. Org. React. 1989, 37, 57.
-
(1983)
Helv. Chim. Acta
, vol.66
, pp. 1655
-
-
Denmark, S.E.1
Weber, E.J.2
-
85
-
-
0023110477
-
-
Calculations indicate similar opportunities for synclinal and anticlinal transition states: Paddon-Row: M. N.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7162. Some examples include: Denmark, S. E.; Weber, E. J. Helv. Chim. Acta 1983, 66, 1655. Danishefsky, S. J.; DeNinno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082. Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293. Fleming, I.; Dunogues, J. Smithers, R. Org. React. 1989, 37, 57.
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 2082
-
-
Danishefsky, S.J.1
DeNinno, S.2
Lartey, P.3
-
86
-
-
0343778881
-
-
Calculations indicate similar opportunities for synclinal and anticlinal transition states: Paddon-Row: M. N.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7162. Some examples include: Denmark, S. E.; Weber, E. J. Helv. Chim. Acta 1983, 66, 1655. Danishefsky, S. J.; DeNinno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082. Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293. Fleming, I.; Dunogues, J. Smithers, R. Org. React. 1989, 37, 57.
-
(1995)
Chem. Rev.
, vol.95
, pp. 1293
-
-
Masse, C.E.1
Panek, J.S.2
-
87
-
-
0002324898
-
-
Calculations indicate similar opportunities for synclinal and anticlinal transition states: Paddon-Row: M. N.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7162. Some examples include: Denmark, S. E.; Weber, E. J. Helv. Chim. Acta 1983, 66, 1655. Danishefsky, S. J.; DeNinno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082. Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293. Fleming, I.; Dunogues, J. Smithers, R. Org. React. 1989, 37, 57.
-
(1989)
Org. React.
, vol.37
, pp. 57
-
-
Fleming, I.1
Dunogues, J.2
Smithers, R.3
-
88
-
-
49049129472
-
-
(a) Guidon, Y.; Morton, H. E.; Yoakim, C. Tetrahedron Lett. 1983, 24, 3969.
-
(1983)
Tetrahedron Lett.
, vol.24
, pp. 3969
-
-
Guidon, Y.1
Morton, H.E.2
Yoakim, C.3
-
89
-
-
0000191147
-
-
(b) Guidon, Y.; Yoakim, C.; Morton, H. E. J. Org. Chem. 1984, 49, 3912.
-
(1984)
J. Org. Chem.
, vol.49
, pp. 3912
-
-
Guidon, Y.1
Yoakim, C.2
Morton, H.E.3
-
90
-
-
12644312578
-
-
Mancuso, A. J.; Huang, S.-H.; Swern, D. J. Org. Chem. 1978, 43, 2480.
-
(1978)
J. Org. Chem.
, vol.43
, pp. 2480
-
-
Mancuso, A.J.1
Huang, S.-H.2
Swern, D.3
-
91
-
-
0000550365
-
-
3 with zinc dust: Freudenberger, J. H.; Konradi, A. W.; Pedersen, S. F. J. Am. Chem. Soc. 1989, 111, 8014.
-
(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 8014
-
-
Freudenberger, J.H.1
Konradi, A.W.2
Pedersen, S.F.3
-
92
-
-
33748230612
-
-
(b) Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 685.
-
(1994)
Angew. Chem., Int. Ed. Engl.
, vol.33
, pp. 685
-
-
Kammermeier, B.1
Beck, G.2
Jacobi, D.3
Jendralla, H.4
-
93
-
-
33845377007
-
-
(c) This complex has been characterized by X-ray crystallography: Cotton, A. F.; Duraj, S. A.; Roth, W. J. Inorg. Chem. 1985, 24, 913.
-
(1985)
Inorg. Chem.
, vol.24
, pp. 913
-
-
Cotton, A.F.1
Duraj, S.A.2
Roth, W.J.3
-
96
-
-
0242666000
-
-
note
-
8alcohol and internal acyl transfer. The X-ray data also confirmed the absolute stereochemistry of 9 arising from the CBS reduction.
-
-
-
-
97
-
-
0242497540
-
-
note
-
9 diketone is most likely due to ring fing strain.
-
-
-
-
98
-
-
33845183759
-
-
(a) McMurry, J. E.; Lectka, T.; Rico, J. G. J. Org. Chem. 1989, 54, 3748.
-
(1989)
J. Org. Chem.
, vol.54
, pp. 3748
-
-
McMurry, J.E.1
Lectka, T.2
Rico, J.G.3
-
101
-
-
84955081239
-
The McMurry reaction
-
Fürstner. A., Ed.; VCH Publishers: New York
-
(d) Lectka, T. The McMurry Reaction. In Active Metals. Preparation, Characterization, Applications; Fürstner. A., Ed.; VCH Publishers: New York, 1995; pp 85-131.
-
(1995)
Active Metals. Preparation, Characterization, Applications
, pp. 85-131
-
-
Lectka, T.1
-
102
-
-
0028849334
-
-
(a) Nicolaou, K. C.; Yang, Z.; Liu, J.-J.; Nantermet, P. G.; Claiborne, C. F.; Renaud, J.; Guy, R. K.; Shibayama, K. J. Am. Chem. Soc. 1995, 117. 645.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 645
-
-
Nicolaou, K.C.1
Yang, Z.2
Liu, J.-J.3
Nantermet, P.G.4
Claiborne, C.F.5
Renaud, J.6
Guy, R.K.7
Shibayama, K.8
-
103
-
-
0025030673
-
-
(b) For other McMurry coupling reactions of diketones and keto aldehydes: McMurry, J. E.; Dushin, R. G. J. Am. Chem. Soc. 1990, 112, 6942.
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 6942
-
-
McMurry, J.E.1
Dushin, R.G.2
-
104
-
-
0032959568
-
-
(c) Mukaiyama, T.; Shiina, I.; Iwadare, H.; Saitoh, M.; Nishimura, T.; Ohkawa, N.; Sakoh, H.; Nishimura, K.; Tani, Y.; Hasegawa, M.; Yamada, K.; Saitoh, K. Chem. Eur. J. 1999, 5, 121.
-
(1999)
Chem. Eur. J.
, vol.5
, pp. 121
-
-
Mukaiyama, T.1
Shiina, I.2
Iwadare, H.3
Saitoh, M.4
Nishimura, T.5
Ohkawa, N.6
Sakoh, H.7
Nishimura, K.8
Tani, Y.9
Hasegawa, M.10
Yamada, K.11
Saitoh, K.12
-
105
-
-
33847798300
-
-
Omura, K.; Sharma, A. K.; Swern, D. J. Org. Chem. 1976, 41, 957.
-
(1976)
J. Org. Chem.
, vol.41
, pp. 957
-
-
Omura, K.1
Sharma, A.K.2
Swern, D.3
-
107
-
-
0242497537
-
Dimethyl sulfoxide-sulfur trioxide/pyridine
-
Paquette, L. A., Ed.: John Wiley and Sons: Chichester, England
-
(b) Tidwell, T. T. Dimethyl Sulfoxide-Sulfur Trioxide/Pyridine. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.: John Wiley and Sons: Chichester, England, 1995; Vol. 3, pp 2156-2157.
-
(1995)
Encyclopedia of Reagents for Organic Synthesis
, vol.3
, pp. 2156-2157
-
-
Tidwell, T.T.1
-
112
-
-
0001491677
-
-
Williams, D. R.; Klingler, F. D.; Dabral, V. Tetrahedron Lett. 1988, 29, 3415.
-
(1988)
Tetrahedron Lett.
, vol.29
, pp. 3415
-
-
Williams, D.R.1
Klingler, F.D.2
Dabral, V.3
-
113
-
-
0242582045
-
-
note
-
We thank Professor Bruce F, Bowden, James Cook University, School of Pharmacy and Molecular Sciences, Queensland 4811, Australia, for providing spectra and COSY NMR data for naturally occurring 1.
-
-
-
|