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34047138762
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Jpn. Kokai Tokkyo Koho, JP 2002047281
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Kimura, J.1
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2
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21244491657
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Review of natural products containing pyrone ring, see: McGlacken G. P., Fairlamb Ian J. S., Nat. Prod. Rep., 22, 369-385 (2005).
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Nat. Prod. Rep
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McGlacken, G.P.1
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3
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22444433706
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Recent report for natural products containing conjugated polyene see
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Recent report for natural products containing conjugated polyene see: Wang F., Luo D.-Q., Liu J.-K., J. Antibiot., 58, 412-415 (2005).
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J. Antibiot
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Wang, F.1
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25144524107
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Recent report for natural products containing conjugated polyene see
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Recent report for natural products containing conjugated polyene see: Igarashi Y., In Y., Ishida T., Fujita T., Yamanaka T., Onaka H., Furumai T., J. Antibiot., 58, 523-525 (2005).
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J. Antibiot
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Igarashi, Y.1
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5
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0347022270
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Recent report for natural products containing conjugated polyene see
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Recent report for natural products containing conjugated polyene see: Weber R. W. S., Muci A., Davoli P., Tetrahedron Lett., 45, 1075-1078 (2004).
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Weber, R.W.S.1
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31944434238
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Review for natural products containing polyene, see
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Review for natural products containing polyene, see: Ishibashi M., Med. Chem., 1, 575-590 (2005).
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Med. Chem
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Ishibashi, M.1
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7
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0036009991
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Review for natural products containing polyene, see
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Review for natural products containing polyene, see: Thirsk C., Whiting A., J. Chem. Soc., Perkin Trans. 1, 2002, 999-1023 (2002).
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J. Chem. Soc., Perkin Trans. 1
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Thirsk, C.1
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0141855265
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Kanai A., Kamino T., Kuramochi K., Kobayashi S., Org. Lett., 5, 2837-2839 (2003).
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Kanai, A.1
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9
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0013300559
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Wang K., Venkataraman H., Kim Y. G., Cha J. K., J. Org. Chem., 56, 7174-7177 (1991).
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J. Org. Chem
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Wang, K.1
Venkataraman, H.2
Kim, Y.G.3
Cha, J.K.4
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10
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34047173392
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Scott W. J., The Stille Reaction in Organic Reactions, 50, Chap. 1, ed. by Paquette L. A., John Willey & Sons, Inc., New York, 1997, pp. 1-652.
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Scott W. J., "The Stille Reaction in Organic Reactions," Vol. 50, Chap. 1, ed. by Paquette L. A., John Willey & Sons, Inc., New York, 1997, pp. 1-652.
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-
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12
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27944498961
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For the aldol reaction of pyrone, see
-
For the aldol reaction of pyrone, see: Kirsch S. F., Bach T., Chem. Eur. J., 11, 7007-7023 (2005).
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(2005)
Chem. Eur. J
, vol.11
, pp. 7007-7023
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Kirsch, S.F.1
Bach, T.2
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13
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0033690703
-
-
For the aldol reaction of pyrone, see:, and references therein. 2000
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For the aldol reaction of pyrone, see: Casiraghi G., Zanardi F., Appendino G., Rassu G., Chem. Rev., 100, 1929-1972 (2000), and references therein.
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(1929)
Chem. Rev
, vol.100
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Casiraghi, G.1
Zanardi, F.2
Appendino, G.3
Rassu, G.4
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14
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0031765407
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For the aldol reaction of pyrone, see
-
For the aldol reaction of pyrone, see: Oikawa H., Kobayashi T., Katayama K., Suzuki Y., Ichihara A., J. Org. Chem., 63, 8748-8756 (1998).
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(1998)
J. Org. Chem
, vol.63
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Oikawa, H.1
Kobayashi, T.2
Katayama, K.3
Suzuki, Y.4
Ichihara, A.5
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15
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0029046854
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For the aldol reaction of pyrone, see
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For the aldol reaction of pyrone, see: Lyga J. W., J. Heterocyclic Chem., 32, 515-518 (1995).
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(1995)
J. Heterocyclic Chem
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Lyga, J.W.1
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16
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0028109279
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For the aldol reaction of pyrone, see
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For the aldol reaction of pyrone, see: Paterson I., Wallace D. J., Tetrahedron Lett., 35, 9477-9480 (1994).
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(1994)
Tetrahedron Lett
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, pp. 9477-9480
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Paterson, I.1
Wallace, D.J.2
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17
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0344580699
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For the aldol reaction of pyrone, see
-
For the aldol reaction of pyrone, see: Munchhof M. J., Heathcock C. H., J. Org. Chem., 59, 7566-7567 (1994).
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(1994)
J. Org. Chem
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Munchhof, M.J.1
Heathcock, C.H.2
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18
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0000499691
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For the aldol reaction of pyrone, see
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For the aldol reaction of pyrone, see: Suh H., Wilcox C. S., J. Am. Chem. Soc., 110, 470-481 (1988).
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(1988)
J. Am. Chem. Soc
, vol.110
, pp. 470-481
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Suh, H.1
Wilcox, C.S.2
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19
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0001309450
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For the aldol reaction of pyrone, see
-
For the aldol reaction of pyrone, see: Ichihara A., Miki M., Tazaki H., Sakamura S., Tetrahedron Lett., 28, 1175-1178 (1987).
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(1987)
Tetrahedron Lett
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Ichihara, A.1
Miki, M.2
Tazaki, H.3
Sakamura, S.4
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20
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0001360042
-
-
For the aldol reaction of pyrone, see
-
For the aldol reaction of pyrone, see: Williams D. R., White F. H., J. Org. Chem., 52, 5067-5079 (1987).
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(1987)
J. Org. Chem
, vol.52
, pp. 5067-5079
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Williams, D.R.1
White, F.H.2
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21
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0142014422
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For the aldol reaction of pyrone, see
-
For the aldol reaction of pyrone, see: Wachter M. P., Harris T. M., Tetrahedron, 26, 1685-1694 (1970).
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(1970)
Tetrahedron
, vol.26
, pp. 1685-1694
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Wachter, M.P.1
Harris, T.M.2
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22
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5144224308
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For the alkylation of pyrone, see
-
For the alkylation of pyrone, see: Doundoulakis T., Xiang A. X., Lira R., Agrios K. A., Webber S. E., Sisson W., Aust R. M., Shah A. M., Showalter R. E., Appleman J. R., Simonsen K. B., Bioorg. Med. Chem. Lett., 14, 5667-5672 (2004).
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Doundoulakis, T.1
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Sisson, W.6
Aust, R.M.7
Shah, A.M.8
Showalter, R.E.9
Appleman, J.R.10
Simonsen, K.B.11
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23
-
-
0024375471
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-
For the alkylation of pyrone, see
-
For the alkylation of pyrone, see: Jones R. C. F., Patience J. M., Tetrahedron Lett., 30, 3217-3218 (1989).
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(1989)
Tetrahedron Lett
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Jones, R.C.F.1
Patience, J.M.2
-
24
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0021838171
-
-
For the alkylation of pyrone, see
-
For the alkylation of pyrone, see: Groutas W. C., Huang T. L., Stanga M. A., Brubaker M. J., Moi M. K., J. Heterocyclic Chem., 22, 433-435 (1985).
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(1985)
J. Heterocyclic Chem
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Groutas, W.C.1
Huang, T.L.2
Stanga, M.A.3
Brubaker, M.J.4
Moi, M.K.5
-
25
-
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34047132597
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Since all protective groups are desirable to be deprotected in one operation at the final step, benzyl group was chosen as the protective group
-
Since all protective groups are desirable to be deprotected in one operation at the final step, benzyl group was chosen as the protective group.
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26
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34047181900
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Direct C-glycosylation of 4-benzyloxy-6-methyl pyrone gave only α-C-glycoside in low yield.
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Direct C-glycosylation of 4-benzyloxy-6-methyl pyrone gave only α-C-glycoside in low yield.
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27
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34047121085
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Protection of the hydroxyl group of pyrone moiety proceeded smoothly to afford the corresponding benzyl ether 7 in 86% yield as a mixture of rotamers under Mitsunobu conditions (DEAD, PPh3 and BnOH).The 1H-NMR (CDCl3 at 25 °C) of benzyl protected pyrone 7 was rather complex, and it seemed to be a mixture of two isomers. However, the 1H-NMR of 7 in DMSO-d6 at 80 °C was gathered and bundled to single isomer. That means that C 3-β-galactopyranosyl-4-benzyloxy-6-methylpyrone might exist as a mixture of rotamer at 25 °C. In contrast, a rotamer was not observed in the case of the corresponding α-isomer
-
3-β-galactopyranosyl-4-benzyloxy-6-methylpyrone might exist as a mixture of rotamer at 25 °C. In contrast, a rotamer was not observed in the case of the corresponding α-isomer.
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29
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34047092652
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The reaction was monitored by TLC analyses before it was quenched, alcohol 12 was major product, however after being quenched, triene 11 was major product. Alcohol 12 has corelation of terminal methyl proton and methine proton of carbon bearing hydroxyl group in the COSY spectrum.
-
The reaction was monitored by TLC analyses before it was quenched, alcohol 12 was major product, however after being quenched, triene 11 was major product. Alcohol 12 has corelation of terminal methyl proton and methine proton of carbon bearing hydroxyl group in the COSY spectrum.
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-
-
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31
-
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0001184408
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and references therein
-
Nishikawa T., Asai M., Ohyabu N., Isobe M., J. Org. Chem., 63, 188-192 (1988), and references therein.
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(1988)
J. Org. Chem
, vol.63
, pp. 188-192
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Nishikawa, T.1
Asai, M.2
Ohyabu, N.3
Isobe, M.4
-
32
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0034750393
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Saito S., Nagahara T., Yamamoto H., Synlett, 2001, 1690-1692 (2001).
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(2001)
Synlett
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, pp. 1690-1692
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Saito, S.1
Nagahara, T.2
Yamamoto, H.3
-
33
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34047178784
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Aldehyde 6 was prepared from pyridinium-1-sulfonate according to the literature, see: Becher J
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Aldehyde 6 was prepared from pyridinium-1-sulfonate according to the literature, see: Becher J., Org. Synth., 59, 79-84 (1979).
-
(1979)
Org. Synth
, vol.59
, pp. 79-84
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-
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34
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15444381139
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Mukaiyama aldol-type reaction using aldehyde 6 was reported, see: Paterson I., Florence G. J., Heimann A. C., Mackay A. C., Angew. Chem. Int. Ed., 44, 1130-1133 (2005).
-
Mukaiyama aldol-type reaction using aldehyde 6 was reported, see: Paterson I., Florence G. J., Heimann A. C., Mackay A. C., Angew. Chem. Int. Ed., 44, 1130-1133 (2005).
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-
-
-
35
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34047130056
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-
3N gave the desired triene 15 only in 30% yield due to competitive retro aldol reaction.
-
3N gave the desired triene 15 only in 30% yield due to competitive retro aldol reaction.
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