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Preliminary communication: Clive, D. L. J.; He, X.; Postema, M. H. D.; Mashimbye, M. J. Tetrahedron Lett. 1998, 39, 4231-4234.
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Clive, D.L.J.1
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33748224042
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4
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0001484549
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Tethered versions of inositol phosphates: Prestwich, G. D. Acc. Chem. Res. 1996, 29, 503-513.
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0027467828
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(a) For an example of an enzymatic resolution, see: Ling, L.; Ozaki, S. Tetrahedron Lett. 1993, 34, 2501-2504. (b) For an example of chemical resolution, see: Aguiló, A.; Martín-Lomas, M.; Penadés, S. Tetrahedron Lett. 1992, 33, 401-404.
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Ling, L.1
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6
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0026551757
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(a) For an example of an enzymatic resolution, see: Ling, L.; Ozaki, S. Tetrahedron Lett. 1993, 34, 2501-2504. (b) For an example of chemical resolution, see: Aguiló, A.; Martín-Lomas, M.; Penadés, S. Tetrahedron Lett. 1992, 33, 401-404.
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Aguiló, A.1
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9
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0000205293
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Sato, K.; Bokura, M.; Taniguchi, M. Bull. Chem. Soc. Jpn. 1994, 67, 1633-1640.
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Sato, K.1
Bokura, M.2
Taniguchi, M.3
-
10
-
-
0345656980
-
-
Tethered versions of 1 have also been made from glucose: see ref 3
-
Tethered versions of 1 have also been made from glucose: see ref 3.
-
-
-
-
12
-
-
0001899585
-
-
Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York
-
Review on ene reaction: Snider, B. B. In Comprehensive Organic Synthesis: Selectivity, Strategy, and Efficiency in Modern Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5, pp 1-27.
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Snider, B.B.1
-
13
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0028106715
-
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For use of an intramolecular pinacol coupling in inositol synthesis, see: (a) Guidot, J. P.; Gall, T. Le; Mioskowskí, C. Tetrahedron Lett. 1994, 35, 6671-6674. (b) Chiara, J. L.; Martín-Lomas, M. Tetrahedron Lett. 1994, 35, 2969-2972.
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Guidot, J.P.1
Le, G.T.2
Mioskowskí, C.3
-
14
-
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0028364675
-
-
For use of an intramolecular pinacol coupling in inositol synthesis, see: (a) Guidot, J. P.; Gall, T. Le; Mioskowskí, C. Tetrahedron Lett. 1994, 35, 6671-6674. (b) Chiara, J. L.; Martín-Lomas, M. Tetrahedron Lett. 1994, 35, 2969-2972.
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Chiara, J.L.1
Martín-Lomas, M.2
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16
-
-
0001378561
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(b) Optically active series: Dreef, C. E.; Tuinman, R. J.; Elie, C. J. J.; van der Marel, G. A.; van Boom, J. H. Recl. Trav. Chim. Pays-Bas 1988, 107, 395-397.
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Dreef, C.E.1
Tuinman, R.J.2
Elie, C.J.J.3
Van Der Marel, G.A.4
Van Boom, J.H.5
-
17
-
-
0344362447
-
-
note
-
2, -78°C: little, if any cyclization product.
-
-
-
-
18
-
-
85082709521
-
-
For related cyclizations involving allyl silanes (with loss of silicon), see: Schinzer, D. Synthesis 1988, 263-273.
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Schinzer, D.1
-
19
-
-
0344794243
-
-
note
-
α,β-Unsaturated ketones incorporating a suitably located propargyl silane unit undergo cyclization with loss of silicon (see ref 16). For a single example of cyclization onto a carbonyl, also with loss of silicon, see ref 17.
-
-
-
-
20
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0001719489
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(a) Schinzer, D.; Dettmer, G.; Ruppelt, M.; Sólyom, S.; Steffen, J. J. Org. Chem. 1988, 53, 3823-3828.
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Schinzer, D.1
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21
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0027048603
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(b) Schinzer, D.; Kabbara, J.; Ringe, K. Tetrahedron Lett. 1992, 33, 8017-8018.
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Schinzer, D.1
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25
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0024455788
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E.g., (a) Asao, K.; Iio, H.; Tokoroyama, T. Tetrahedron Lett. 1989, 30, 6397-6400.
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Asao, K.1
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27
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0012941308
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-
For intermolecular reactions of propargyl silanes with electrophiles, see: (a) Pornet, J.; Aubert, P.; Randrianoélina, B.; Miginiac, L. Tetrahedron Lett. 1984, 25, 651-654. (b) Pornet, J.; Randrianoélina, B.; Miginiac, L. J. Organomet. Chem. 1994, 481, 217-225.
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Pornet, J.1
Aubert, P.2
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Miginiac, L.4
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28
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-
0345656975
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-
For intermolecular reactions of propargyl silanes with electrophiles, see: (a) Pornet, J.; Aubert, P.; Randrianoélina, B.; Miginiac, L. Tetrahedron Lett. 1984, 25, 651-654. (b) Pornet, J.; Randrianoélina, B.; Miginiac, L. J. Organomet. Chem. 1994, 481, 217-225.
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Pornet, J.1
Randrianoélina, B.2
Miginiac, L.3
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29
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0001453658
-
-
For cyclizations of allenyl silanes that occur with retention of silicon, and for which the presence of the silicon substituent is essential, see: (a) Jin, J.; Smith, D. T.; Weinreb, S. M. J. Org. Chem. 1995, 60, 5366-5367. (b) Weinreb, S. M.; Smith, D. T.; Jin, J. Synthesis 1998, 509-521. Cf. Esch, P. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1988, 29, 367-370.
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Jin, J.1
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Weinreb, S.M.3
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30
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-
0031776141
-
-
For cyclizations of allenyl silanes that occur with retention of silicon, and for which the presence of the silicon substituent is essential, see: (a) Jin, J.; Smith, D. T.; Weinreb, S. M. J. Org. Chem. 1995, 60, 5366-5367. (b) Weinreb, S. M.; Smith, D. T.; Jin, J. Synthesis 1998, 509-521. Cf. Esch, P. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1988, 29, 367-370.
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Weinreb, S.M.1
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31
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0001726491
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For cyclizations of allenyl silanes that occur with retention of silicon, and for which the presence of the silicon substituent is essential, see: (a) Jin, J.; Smith, D. T.; Weinreb, S. M. J. Org. Chem. 1995, 60, 5366-5367. (b) Weinreb, S. M.; Smith, D. T.; Jin, J. Synthesis 1998, 509-521. Cf. Esch, P. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1988, 29, 367-370.
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Esch, P.M.1
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Fukase, K.; Matsumoto, T.; Ito, N.; Yoshimura, T.; Kotani, S.; Kusumoto, S. Bull. Chem. Soc. Jpn. 1992, 65, 2643-2654.
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Fukase, K.1
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Ito, N.3
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Kotani, S.5
Kusumoto, S.6
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33
-
-
0345656974
-
-
note
-
Exploratory studies guided our choice of allyl glycosides, as we found indications that hydrolysis of methyl glycosides was not possible without loss of p-methoxybenzyl groups (which we wished to use for protection of two of the hydroxyls).
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37
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0028225956
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Grandjean, D.; Pale, P.; Chuche, J. Tetrahedron Lett. 1994, 35, 3529-3530.
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Grandjean, D.1
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Chuche, J.3
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39
-
-
0345656972
-
-
note
-
2, -78°C: some cyclization (<39%) probably occurred.
-
-
-
-
40
-
-
0345656970
-
-
2, PDC, PCC, Swern, TPAP-NMO
-
2, PDC, PCC, Swern, TPAP-NMO.
-
-
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42
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33747176412
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(b) Luche, J.-L.; Rodriguez-Hahn, L.; Crabbé, P. J. Chem. Soc., Chem. Commun. 1978, 601-602.
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Luche, J.-L.1
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43
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0000590383
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Cf. (a) Slomp, G.; Jr.; Johnson, J. L. J. Am. Chem. Soc. 1958, 80, 915-921. (b) Boddy, I. K.; Boniface, P. J.; Cambie, R. C.; Craw, P. A.; Huang, Z.-D.; Larsen, D. S.; McDonald, H.; Rutledge, P. S.; Woodgate, P. D. Aust. J. Chem. 1984, 37, 1511-1529.
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Slomp G., Jr.1
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44
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84970556070
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Cf. (a) Slomp, G.; Jr.; Johnson, J. L. J. Am. Chem. Soc. 1958, 80, 915-921. (b) Boddy, I. K.; Boniface, P. J.; Cambie, R. C.; Craw, P. A.; Huang, Z.-D.; Larsen, D. S.; McDonald, H.; Rutledge, P. S.; Woodgate, P. D. Aust. J. Chem. 1984, 37, 1511-1529.
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Boddy, I.K.1
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McDonald, H.7
Rutledge, P.S.8
Woodgate, P.D.9
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45
-
-
0025108083
-
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1H NMR) of the desired equatorial alcohol. For relevant examples of reduction to equatorial alcohols, see: (a) Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001-7031. (b) Corey, E. J.; Hopkins, P. B.; Kim, S.; Yoo, S.-e.; Nambiar, K. P.; Falck, J. R. J. Am. Chem. Soc. 1979, 101, 7131-7134.
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Evans, D.A.1
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Stout, T.J.5
-
46
-
-
0018569298
-
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1H NMR) of the desired equatorial alcohol. For relevant examples of reduction to equatorial alcohols, see: (a) Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001-7031. (b) Corey, E. J.; Hopkins, P. B.; Kim, S.; Yoo, S.-e.; Nambiar, K. P.; Falck, J. R. J. Am. Chem. Soc. 1979, 101, 7131-7134.
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Corey, E.J.1
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Falck, J.R.6
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47
-
-
0344362435
-
-
note
-
3P) each gave a trace of the desired products. Use of KONO, 18-crown-6 in DMF, followed by water at reflux, gave the equatorial alcohol in about 40% yield. The system was prone to dehydration under Mitsunobu conditions.
-
-
-
-
48
-
-
0344362434
-
-
Sawyer, A. K., Ed.; Dekker: New York,
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Radical stannane reduction of ketones has been reported, but is not an established synthetic method: Cf. (a) Kupchik, E. J. In Organotin Compounds; Sawyer, A. K., Ed.; Dekker: New York, , 1971; p 49. (b) Kuivila, H. G. Synthesis 1970, 499-509.
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49
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85034181424
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Radical stannane reduction of ketones has been reported, but is not an established synthetic method: Cf. (a) Kupchik, E. J. In Organotin Compounds; Sawyer, A. K., Ed.; Dekker: New York, , 1971; p 49. (b) Kuivila, H. G. Synthesis 1970, 499-509.
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Kuivila, H.G.1
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33751391619
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(a) For use of propargyl silanes in biomimetic polyene cyclizations, see: Johnson, W. S.; Plummer, M. S.; Pulla Reddy, S.; Bartlett, W. R. J. Am. Chem. Soc. 1993, 115, 515-521. (b) For use of iminium ions in the cyclization of propargyl silanes, see: Fischer, M. J.; Overman, L. E. J. Org. Chem. 1990, 55, 1447-1459.
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(a) For use of propargyl silanes in biomimetic polyene cyclizations, see: Johnson, W. S.; Plummer, M. S.; Pulla Reddy, S.; Bartlett, W. R. J. Am. Chem. Soc. 1993, 115, 515-521. (b) For use of iminium ions in the cyclization of propargyl silanes, see: Fischer, M. J.; Overman, L. E. J. Org. Chem. 1990, 55, 1447-1459.
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