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1
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0035743164
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Simoni D., Rondanin R., Baruchello R., Roberti M., Rossi M., Grimaudo S., D'Alessandro N., Invidiata F.P., Tolomeo M. Pure Appl. Chem. 73:2001;1437
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(2001)
Pure Appl. Chem.
, vol.73
, pp. 1437
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Simoni, D.1
Rondanin, R.2
Baruchello, R.3
Roberti, M.4
Rossi, M.5
Grimaudo, S.6
D'Alessandro, N.7
Invidiata, F.P.8
Tolomeo, M.9
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3
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0035525766
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Cassinat B., Chevert S., Zassadowski F., Balitrand N., Guillemot I., Menot L., Degos L., Fenaux P., Chomienne C. Blood. 98:2001;2862
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(2001)
Blood
, vol.98
, pp. 2862
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Cassinat, B.1
Chevert, S.2
Zassadowski, F.3
Balitrand, N.4
Guillemot, I.5
Menot, L.6
Degos, L.7
Fenaux, P.8
Chomienne, C.9
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4
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3042669499
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Eur. Patent Appl. No 728742, 1996
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For a derivative of 9-cis retinoic acid in which iodine substitutes a vinylic hydrogen see: Klaus, M.; Lovey, A. J.; Mohr, P.; Rosenberg, M. Eur. Patent Appl. No 728742, 1996
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Klaus, M.1
Lovey, A.J.2
Mohr, P.3
Rosenberg, M.4
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5
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0037430575
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This compound has recently been obtained by a free-radical approach; see:
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This compound has recently been obtained by a free-radical approach; see: Commeiras L., Santelli M., Parrain J.-L. Tetrahedron Lett. 44:2003;2311
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(2003)
Tetrahedron Lett.
, vol.44
, pp. 2311
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Commeiras, L.1
Santelli, M.2
Parrain, J.-L.3
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6
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0035838855
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MacMahon S., Fong R., Baran P.S., Safonov I., Wilson S.R., Schuster D.I. J. Org. Chem. 66:2001;5449
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(2001)
J. Org. Chem.
, vol.66
, pp. 5449
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MacMahon, S.1
Fong, R.2
Baran, P.S.3
Safonov, I.4
Wilson, S.R.5
Schuster, D.I.6
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7
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0001034015
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Red-Al has been shown to be the reagent of choice for this transformation:
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Red-Al has been shown to be the reagent of choice for this transformation: Denmark S.E., Jones T.K. J. Org. Chem. 47:1982;4595
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(1982)
J. Org. Chem.
, vol.47
, pp. 4595
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Denmark, S.E.1
Jones, T.K.2
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8
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0024406910
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for related examples see:
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for related examples see: Blanchette M.A., Malamas M.S., Nantz M.H., Roberts J.C., Somfai P., Whritenour D.C., Masamune S. J. Org. Chem. 54:1989;2817
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(1989)
J. Org. Chem.
, vol.54
, pp. 2817
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Blanchette, M.A.1
Malamas, M.S.2
Nantz, M.H.3
Roberts, J.C.4
Somfai, P.5
Whritenour, D.C.6
Masamune, S.7
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11
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0030199618
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The Z configuration of
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The Z configuration of 3 has been secured by its conversion to nakienone B. See: Pour M., Negishi E.-I. Tetrahedron Lett. 37:1996;4679
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(1996)
Tetrahedron Lett.
, vol.37
, pp. 4679
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Pour, M.1
Negishi, E.-I.2
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13
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3042625197
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note
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3), 72.3 (C-4), 128.8 (C-3), 129.1(C-2), 196.5 (C-1) can be purified by column chromatography but should be freshly prepared before use
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15
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3042574144
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note
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3), 71.7 (C-8), 111.7 (C-7), 120.6 (C-2), 131.1, 135.1, 138.8 (C-4, C-5, C-6), 151.7 (C-3), 166.8 (C-1)
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16
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3042527751
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note
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In contrast to oxidation of 3, the use of IBX resulted here in configurational scrambling as a 1:1.8 E/Z mixture was detected
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21
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0035925006
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Crombie B.S., Smith C., Varnavas C.Z., Wallace T.W. J. Chem. Soc., Perkin Trans. 1. 2001;206
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(2001)
J. Chem. Soc., Perkin Trans. 1
, pp. 206
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Crombie, B.S.1
Smith, C.2
Varnavas, C.Z.3
Wallace, T.W.4
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22
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3042625198
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3-1), 33.2 (C-4), 34.3 (C-1), 39.7 (C-2), 124.7 (C-13), 127.0, 128.6, 128.7, 130.5, 145.2 (C-7, C-10, C-11, C-12, C-14), 130.9 (C-5), 137.0 (C-8), 137.6 (C-6), 143.6 (C-9), 168.0 (C-15)
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(1988)
Z. Naturforsch.
, vol.43 B
, pp. 1072
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Perly, B.1
Pappalardo, G.C.2
Klaus, M.3
Montoneri, E.4
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23
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0021025690
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3-1), 33.2 (C-4), 34.3 (C-1), 39.7 (C-2), 124.7 (C-13), 127.0, 128.6, 128.7, 130.5, 145.2 (C-7, C-10, C-11, C-12, C-14), 130.9 (C-5), 137.0 (C-8), 137.6 (C-6), 143.6 (C-9), 168.0 (C-15)
-
(1983)
J. Org. Chem.
, vol.48
, pp. 3164
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Bernard, M.1
Ford, W.T.2
Nelson, E.C.3
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24
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3042669497
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note
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3-1), 33.2 (C-4), 34.3 (C-1), 39.7 (C-2), 124.7 (C-13), 127.0, 128.6, 128.7, 130.5, 145.2 (C-7, C-10, C-11, C-12, C-14), 130.9 (C-5), 137.0 (C-8), 137.6 (C-6), 143.6 (C-9), 168.0 (C-15)
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27
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0000991678
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O-TMS propargyl alcohol is very moisture sensitive and was directly used after in situ formation that is without isolation. For use of a tert-butyldimethylsilyl ether, see:
-
O-TMS propargyl alcohol is very moisture sensitive and was directly used after in situ formation that is without isolation. For use of a tert-butyldimethylsilyl ether, see: Piers E., Chong M., Morton H.E. Tetrahedron. 45:1989;363
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(1989)
Tetrahedron
, vol.45
, pp. 363
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Piers, E.1
Chong, M.2
Morton, H.E.3
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30
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3042669498
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note
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Under those conditions, NMR analysis of the crude material showed 92% E configurational purity; note that a 6 to 4:1 E/Z ratio was observed after reaction with the ylide derived from 9 (see Ref. 19)
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31
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37049069183
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For the elimination of iodine in such a conjugated ester, see:
-
For the elimination of iodine in such a conjugated ester, see: Brisdon B.J., Brown D.W., Willis C.R., Drew M.G.B. J. Chem. Soc., Dalton Trans. 1986;2405
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(1986)
J. Chem. Soc., Dalton Trans.
, pp. 2405
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Brisdon, B.J.1
Brown, D.W.2
Willis, C.R.3
Drew, M.G.B.4
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32
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3042530121
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note
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The less toxic bis(tributyl)ditin was ineffective for this transformation
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33
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3042571787
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note
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2/Pd (0), 73%); 2 could be regenerated (90%) after reaction with iodine
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