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1
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37349016936
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For total syntheses already published, see: A. Fürstner, L.C. Bouchez, J.-A. Funel, V. Liepins, F.-H. Poree, R. Gilmour, F. Beaufils, D. Laurich, and M. Tamiya Angew. Chem., Int. Ed. 46 2007 9265 9270
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Fürstner, A.1
Bouchez, L.C.2
Funel, J.-A.3
Liepins, V.4
Poree, F.-H.5
Gilmour, R.6
Beaufils, F.7
Laurich, D.8
Tamiya, M.9
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3
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65349119947
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A. Fürstner, L.C. Bouchez, L. Morency, J.-A. Funel, V. Liepins, F.-H. Poree, R. Gilmour, D. Laurich, F. Beaufils, and M. Tamiya Chem. Eur. J. 15 2009 3983 4010
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Fürstner, A.1
Bouchez, L.C.2
Morency, L.3
Funel, J.-A.4
Liepins, V.5
Poree, F.-H.6
Gilmour, R.7
Laurich, D.8
Beaufils, F.9
Tamiya, M.10
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4
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0023010701
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A.G.M. Barrett, R.A.E. Carr, S.V. Attwood, G. Richardson, and N.D.A. Walshe J. Org. Chem. 51 1986 4840 4856
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Richardson, G.4
Walshe, N.D.A.5
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5
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0026325277
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By means of a Still-Gennari reaction from (2S)-2-(tetrahydro-pyran-2- yloxy)propanal, with ethyl 2-[bis(2,2,2-trifluoroethoxy) phosphinyl]propanoate prepared according to: C. Patois, and P. Savignac Synth. Commun. 21 1991 2391 2396
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Patois, C.1
Savignac, P.2
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6
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4143120630
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-
3 in agreement with: S.-K. Kang, and D.-H. Lee Synlett 1991 175 176 Reduction with DIBALH in THF at -78 °C afforded the lactol (1′/1″) in good yield
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Synlett
, pp. 175-176
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Kang, S.-K.1
Lee, D.-H.2
-
7
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77949510034
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For representative examples, see: L. Shi, X. Lei, J. Zhang, and G. Lin Helv. Chim. Acta 93 2010 555 564
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Shi, L.1
Lei, X.2
Zhang, J.3
Lin, G.4
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11
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0000914258
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-
For a classical review, see: R.D. Little, M.R. Masjedizadeh, O. Wallquist, and J.I. McLoughlin Org. React. 47 1995 315 552
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Little, R.D.1
Masjedizadeh, M.R.2
Wallquist, O.3
McLoughlin, J.I.4
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18
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71849107169
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S.F. Jenkinson, K.V. Booth, A.M. Estévez-Reino, G. Horne, R.J. Estévez, and G.W.J. Fleet Tetrahedron: Asymmetry 20 2009 2357 2367
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Jenkinson, S.F.1
Booth, K.V.2
Estévez-Reino, A.M.3
Horne, G.4
Estévez, R.J.5
Fleet, G.W.J.6
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21
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70350741286
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a value in DMSO of 18.6. It means that the basicity of the HWE reagent (the anion) is ca. 10 units stronger than that of the sW reagent. See: C. Qi, Y. Du, Y. Lu, X. Sun, and X.-M. Zhang J. Org. Chem. 74 2009 8078 8085
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J. Org. Chem.
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, pp. 8078-8085
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Qi, C.1
Du, Y.2
Lu, Y.3
Sun, X.4
Zhang, X.-M.5
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23
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80052310167
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also see: http://www.chem.wisc.edu/areas/reich/pkatable/kaphos.gif.
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24
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0000755224
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One oxolane stereoisomer was formed mainly in each case, as depicted in Table 1, with the side chain at C2 and Me at C3 in trans. Ratios 3a/3a′ and 3d/3d′ were between 90:10 and 95:5. The relative configuration of 3a was assigned by NOESY experiments and by comparison with available NMR data of very similar structures: M.F. Semmelhack, and N. Zhang J. Org. Chem. 54 1989 4483 4485
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Semmelhack, M.F.1
Zhang, N.2
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27
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67749147299
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for the relative nucleophilicities of P-stabilised carbanions, see: R. Appel, R. Loos, and H. Mayr J. Am. Chem. Soc. 131 2009 704 714
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Appel, R.1
Loos, R.2
Mayr, H.3
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28
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25444458327
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also see the following papers and references therein: L.K. Blasdel, and A.G. Myers Org. Lett. 7 2005 4281 4283 (use of fluorinated alkoxides)
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Org. Lett.
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Blasdel, L.K.1
Myers, A.G.2
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29
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1542328778
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C. Bonini, L. Chiummiento, M. De Bonnis, M. Funicello, and P. Lupattelli Tetrahedron Lett. 45 2004 2797 2799
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Bonini, C.1
Chiummiento, L.2
De Bonnis, M.3
Funicello, M.4
Lupattelli, P.5
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0035945995
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J. Motoyoshiya, T. Kusaura, K. Kokin, S. Yokoya, Y. Takaguchi, S. Narita, and H. Aoyama Tetrahedron 57 2001 1715 1721
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Motoyoshiya, J.1
Kusaura, T.2
Kokin, K.3
Yokoya, S.4
Takaguchi, Y.5
Narita, S.6
Aoyama, H.7
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33
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0025353787
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An alternative approach may be suggested, based on a suitable opening of lactol 1′/1″, followed by the protection of the hydroxy group and a standard HWE reaction with the CHO group once deprotected, but it meant additional synthetic steps. The direct protection of the hydroxy group is sometimes appropriate for lactols not substituted at C5, the open form of which is a more reactive primary alcohol (in general, when the OH group of the open form is less congested than the OH group of the lactol): E.K. Yau, and J.K. Coward J. Org. Chem. 55 1990 3147 3158
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0038056114
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R. Sibley, H. Hatoum-Mokdad, R. Schoenleber, L. Musza, W. Stirtan, D. Marrero, W. Carley, H. Xiao, and J. Dumas Bioorg. Med. Chem. Lett. 13 2003 1919 1922
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Schoenleber, R.3
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Stirtan, W.5
Marrero, D.6
Carley, W.7
Xiao, H.8
Dumas, J.9
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36
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75149112252
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W.H. Kim, A.-Y. Park, J.-A. Kang, J. Kim, J.-A. Kim, H.-R. Lee, P. Chun, J. Choi, C.-K. Lee, L.S. Jeong, and H.R. Moon Tetrahedron 66 2010 1706 1715
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Kim, W.H.1
Park, A.-Y.2
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Lee, H.-R.6
Chun, P.7
Choi, J.8
Lee, C.-K.9
Jeong, L.S.10
Moon, H.R.11
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73449093181
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T.J.A. Graham, E.E. Gray, J.M. Burgess, and B.C. Goess J. Org. Chem. 75 2010 226 228 However, in the case of 1′/1″, different attempts (with LiHMDS in THF at -78 °C followed after equilibration by addition of TBSCl and warming up to rt, with LiHMDS and TBSCl by direct mixing in THF at rt, with KHMDS at -78 °C and heating later at 60 °C with TBDPSCl) led to the TBS- or TBDPS-protected cyclic form (lactol) as the major product
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Graham, T.J.A.1
Gray, E.E.2
Burgess, J.M.3
Goess, B.C.4
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20544462132
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Preparation: J.A. Grzyb, M. Shen, C. Yoshina-Ishii, W. Chi, R.S. Brown, and R.A. Batey Tetrahedron Lett. 61 2005 7153 7175
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Batey, R.A.6
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44
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0042698526
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2OH as a protic co-solvent in another context, see: O. Arjona, R. Medel, J. Rojas, A.M. Costa, and J. Vilarrasa Tetrahedron Lett. 44 2003 6369 6373
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Medel, R.2
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Vilarrasa, J.5
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46
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0037164673
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We have been unable to find examples of opening of five-membered lactols with such a phosphorane, but there is one from a six-membered lactol: S. Nakamura, J. Inagaki, T. Sugimoto, Y. Ura, and S. Hashimoto Tetrahedron 58 2002 10375 10386
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Sugimoto, T.3
Ura, Y.4
Hashimoto, S.5
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47
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68749089734
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Besides, the E selectivity is higher. The trend of the Weinreb amides of sW, HWE and Ando reagents to afford higher selectivities than the corresponding E or Z esters is known: K. Ando, S. Nagaya, and Y. Tarumi Tetrahedron Lett. 50 2009 5689 5691 and Ref. 10 cited therein; morpholine amides of Ando reagents also give higher Z/E ratios
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Ando, K.1
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Tarumi, Y.3
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R. Martín, P. Romea, C. Tey, F. Urpí, and J. Vilarrasa Synlett 1997 1414 1416
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Martín, R.1
Romea, P.2
Tey, C.3
Urpí, F.4
Vilarrasa, J.5
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