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0001524453
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The first total synthesis generated a mixture of denticulatin A and B, see: Ziegler, F. E.; Becker, M. R. J. Org. Chem. 1990, 55, 2800.
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For the first stereoselective synthesis of denticulatin B, see: Paterson, I.; Perkins, M. V. Tetrahedron 1996, 52, 1811.
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(a) For a preliminary communication, see: Oppolzer, W.; De Brabander, J.; Walther, E.; Bernardinelli, G. Tetrahedron Lett. 1995, 36, 4413.
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(a) Reviews dealing with chain desymmetrizations: Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9; Magnuson, S. R. Tetrahedron 1995, 51, 2167.
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(a) Reviews dealing with chain desymmetrizations: Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9; Magnuson, S. R. Tetrahedron 1995, 51, 2167.
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Magnuson, S.R.1
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26
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0029938866
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(b) For an elegant approach towards the synthesis of polypropionate fragments via a kinetic desymmetrization of polycyclic systems, see: Marchionni, C.; Vogel, P.; Roversi, P. Tetrahedron Lett. 1996, 37, 4149.
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Marchionni, C.1
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27
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0001579832
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Preparation of meso dialdehyde 6 and its desymmetrization by olefination with a chiral phosphonate: Kann, N.; Rein, T. J. Org. Chem. 1993, 58, 3802.
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Kann, N.1
Rein, T.2
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28
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0343883866
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Prepared according to ref. 12
-
Prepared according to ref. 12.
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29
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0000784039
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and references cited therein
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Roush, W. R. J. Org. Chem. 1991, 56, 4151 and references cited therein.
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Roush, W.R.1
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30
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0031028094
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The same strategy was very recently applied by us towards a very short synthesis of the Prelog-Djerassi lactonic acid: Oppolzer, W.; Walther, E.; Balado, C. P.; De Brabander, J. Tetrahedron Lett. 1997, 38, 809.
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Oppolzer, W.1
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31
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0000282109
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The formation of thioglycosides with 1,2-ethanedithiol in this type of reaction has been observed previously: (a) Askin, D.; Angst, C.; Danishefsky, S. J. Org. Chem. 1987, 52, 622.
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Ferro, V.1
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34
-
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0343883864
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note
-
Changing to organocerium compounds or adding HMPA or TMEDA to the reaction medium did not have any effect on the addition.
-
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36
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84953502363
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Levin, J. I.; Turos, E.; Weinreb, S. M. Synth. Commun. 1982, 12, 989.
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37
-
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0343448003
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note
-
Reduction with diisobutylaluminum hydride or lithium aluminumhydride gave concomminant deprotection of the silyl protecting group.
-
-
-
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39
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0342538231
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Miyata, O.; Fujiwara, Y.; Nishiguchi, A.; Honda, H.; Shinada, T.; Ninomiya, I.; Naito, T. Synlett 1994, 637.
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(a) Cardellicchio, C.; Fiandanese, V.; Marchese, G.; Ronzini, L. Tetrahedron Lett. 1985, 26, 3595.
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(b) Viandanese, V.; Marchese, G.; Naso, F. ibid. 1988, 29, 3587.
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Viandanese, V.1
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42
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0005691124
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submitted
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For a full account of the scope and limitations for this two step transformation of N-acylbornane-10,2-sultams into optically pure ketones: Oppolzer, W.; Darcel, C.; Rochet, P.; Rosset, S.; De Brabander, J. Helv. Chim. Acta, submitted.
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Helv. Chim. Acta
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Oppolzer, W.1
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(b) Oppolzer, W.; Rodriguez, I.; Starkemann, C.; Walther, E. ibid. 1990, 31, 5019.
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Oppolzer, W.1
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46
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0343012446
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note
-
7 They describe the synthesis of aldehyde 3 in 80% ee, via alcohol 26 obtained from kinetically resolved (R)-2-methyl-1-penten-3-ol. Furthermore, a sample of 26 oxidized to aldehyde 3 with pyridinium chlorochromate and reduced back to the same alcohol showed no racemization during this process.
-
-
-
-
47
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84958315401
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The chlorotitanium enolates were generated by the standard procedure reported by: Evans, D. A.; Rieger, D. L.; Bilodeau, M. T.; Urpí, F. J. Am. Chem. Soc. 1991, 113, 1047. These substrates exhibit the stereochemical attributes of Z(O)-enolates.
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Evans, D.A.1
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Bilodeau, M.T.3
Urpí, F.4
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48
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33947085164
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House, H. O.; Crumrine, D. S.; Teranishi, A. Y.; Olmstead, H. D. J. Am. Chem. Soc. 1973, 95, 3310 and references cited therein.
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49
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Evans, D. A.; Ng, H. P.; Rieger, D. L. J. Am. Chem. Soc. 1993, 115, 11446.
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50
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and references cited therein
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(a) Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G.; Livingston, A. B. J. Am. Chem. Soc. 1995, 117, 6619 and references cited therein.
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51
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0000730312
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and references cited therein
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(b) Evans, D. A.; Dart, M. J.; Duffy, J. L.; Rieger, D. L. ibid. 1995, 117, 9073 and references cited therein.
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52
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0001051059
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and references cited therein
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(c) Evans, D. A.; Yang, M. G.; Dart, M. J.; Duffy, J. L.; Kim, A. S. ibid. 1995, 117, 9598 and references cited therein.
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Evans, D.A.1
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53
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15844376790
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and references cited therein
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(d) Evans, D. A.; Dart, M. J.; Duffy, M. J.; Yang, M. G. ibid. 1996, 118, 4322 and references cited therein.
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Evans, D.A.1
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Yang, M.G.4
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54
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0343883861
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note
-
It was mentioned that also the nature of the protecting group of the β-oxygen bearing substituent plays a significant role, giving an attenuation of 1,3-stereoinduction with a t-butyldimethylsilyl protecting group relative to a p-methoxybenzyl ether: see ref. 31b.
-
-
-
-
55
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0343012443
-
-
note
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We are indebted to Dr. Ian Paterson for kindly providing reference spectra and experimental details.
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-
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58
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0343447999
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note
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7
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