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a) Lignans, Ayres, D. C.; Loike, J. D., Ed.; Cambridge University Press: New York, 1990.
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Lignans, A.D.C.1
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5
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0025080417
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Review on asymmetric synthesis of lignans: Ward, R. S. Tetrahedron 1990, 46, 5029.
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Ward, R.S.1
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Tomioka, K; Mizuguchi, H.; Koga, K. Chem. Pharm. Bull. 1982, 30, 4304.
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a) Oeveren, A.; Jansen, J. F. G. A.; Feringa, B. L. J. Org. Chem. 1994, 59, 5999.
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Feringa, B.L.3
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37049089501
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b) Pelter, A.; Ward, R. S.; Jones, D. M.; Maddocks, P. J. Chem. Soc., Perkin Trans. 1 1993, 2631.
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Pelter, A.1
Ward, R.S.2
Jones, D.M.3
Maddocks, P.4
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d) Speybroek, R. V.; Guo. H.; Eycken, J. V.; Vandewalle, M. Tetrahedron 1991, 47, 4675.
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Speybroek, R.V.1
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b) Pelter, A.; Ward, R. S.; Qianrong, L.; Pis, J. Tetrahedron: Asymmetry 1994, 5, 909.
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Tetrahedron: Asymmetry
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Pelter, A.1
Ward, R.S.2
Qianrong, L.3
Pis, J.4
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14
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0029904857
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d) Berkowitz, D. B.; Maeng, J.; Dantzig, A. H.; Shepard, R. L.; Norman, B. H. J. Am. Chem. Soc. 1996, 118, 9426.
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Berkowitz, D.B.1
Maeng, J.2
Dantzig, A.H.3
Shepard, R.L.4
Norman, B.H.5
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Andrews, R. C.; Teague, S. J.; Meyers, A. I. J. Am. Chem. Soc. 1988, 110, 7854.
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Andrews, R.C.1
Teague, S.J.2
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16
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0024994611
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Ogiku, T.; Seki, M.; Takahashi, M.; Ohmizu, H.; Iwasaki, T. Tetrahedron Lett. 1990, 31, 5487.
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Ogiku, T.1
Seki, M.2
Takahashi, M.3
Ohmizu, H.4
Iwasaki, T.5
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0342520664
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b) Ogiku, T.; Yoshida, S.; Kuroda, T.; Ohmizu, H.; Iwasaki, T. Synlett 1992, 651.
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Synlett
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Ogiku, T.1
Yoshida, S.2
Kuroda, T.3
Ohmizu, H.4
Iwasaki, T.5
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18
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0027073264
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c) Ogiku, T.; Yoshida, S.; Takahashi, M.; Kuroda, T.; Ohmizu, H.; Iwasaki, T. Bull. Chem. Soc., Jpn. 1992, 65, 3495.
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Bull. Chem. Soc., Jpn.
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Ogiku, T.1
Yoshida, S.2
Takahashi, M.3
Kuroda, T.4
Ohmizu, H.5
Iwasaki, T.6
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19
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33751154396
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(d) Ogiku, T.; Yoshida, S.; Ohmizu, H.; Iwasaki, T. J. Org. Chem. 1995, 60, 4585.
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Ogiku, T.1
Yoshida, S.2
Ohmizu, H.3
Iwasaki, T.4
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0026695669
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(e) Ogiku, T.; Yoshida, S.; Takahashi, M.; Kuroda, T.; Ohmizu, H.; Iwasaki, T. Tetrahedron Lett. 1992, 33, 4473.
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Tetrahedron Lett.
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, pp. 4473
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Ogiku, T.1
Yoshida, S.2
Takahashi, M.3
Kuroda, T.4
Ohmizu, H.5
Iwasaki, T.6
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21
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0026637882
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(f) Ogiku, T.; Yoshida, S.; Takahashi, M.; Kuroda, T.; Ohmizu, H.; Iwasaki, T. Tetrahedron Lett. 1992, 33, 4477.
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Tetrahedron Lett.
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, pp. 4477
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Ogiku, T.1
Yoshida, S.2
Takahashi, M.3
Kuroda, T.4
Ohmizu, H.5
Iwasaki, T.6
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22
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0028918730
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(g) Ogiku, T.; Yoshida, S.; Ohmizu, H.; Iwasaki, T. J. Org. Chem. 1995, 60, 1148.
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J. Org. Chem.
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Ogiku, T.1
Yoshida, S.2
Ohmizu, H.3
Iwasaki, T.4
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23
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0001392802
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(h) Yoshida, S.; Ogiku, T.; Ohmizu, H.; Iwasaki, T. J. Org. Chem. 1997, 62, 1310.
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(1997)
J. Org. Chem.
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Yoshida, S.1
Ogiku, T.2
Ohmizu, H.3
Iwasaki, T.4
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24
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0029090888
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For preliminary reports, see: Yoshida, S.; Yamanaka, T.; Miyake, T.; Moritani, Y.; Ohmizu, H.; Iwasaki, T. Tetrahedron Lett. 1995, 36, 7271.
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(1995)
Tetrahedron Lett.
, vol.36
, pp. 7271
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Yoshida, S.1
Yamanaka, T.2
Miyake, T.3
Moritani, Y.4
Ohmizu, H.5
Iwasaki, T.6
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25
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0000144488
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(a) Matsunaga, H.; Sakamaki, T.; Nagaoka, H.; Yamada, Y. Tetrahedron Lett. 1983, 29, 3009.
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(1983)
Tetrahedron Lett.
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Matsunaga, H.1
Sakamaki, T.2
Nagaoka, H.3
Yamada, Y.4
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26
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0001233216
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(b) Minami, N.; Ko, S. S.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 1109.
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J. Am. Chem. Soc.
, vol.104
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Minami, N.1
Ko, S.S.2
Kishi, Y.3
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27
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33751498908
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These chiral aldehydes 8 and 9 can be easily prepared from the commercially available 1,2:5,6-diisopropylidene-D-mannitol and 5,6-O-isopropylidene-L-gulono-1,4-lactone in one step: a) Schmid, C. R.; Bryant, J. D.; Dowlatzedah, M.; Phillips, J. L.; Prather, D. E.; Schantz, R. E.; Sear, N. L.; Vianco, C. S. J. Org. Chem. 1991, 56, 4056.
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J. Org. Chem.
, vol.56
, pp. 4056
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Schmid, C.R.1
Bryant, J.D.2
Dowlatzedah, M.3
Phillips, J.L.4
Prather, D.E.5
Schantz, R.E.6
Sear, N.L.7
Vianco, C.S.8
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29
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84889544137
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note
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8c By using this method, 4 and 12 were converted into 13 and 14 quantitatively.
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30
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84889546779
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note
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Crystal data for 14 has been deposited at the Cambridge Crystallographic Data Centre.
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31
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37049089733
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Addition of HMPA in the Michael addition reaction of α-alkyl β-keto esters via chiral enarnines has been reported to improve diastereoselectivity: Ando, K.; Yasuda, K.; Tomioka, K.; Koga, K. J. Chem. Soc., Perkin Trans. 1 1994, 277.
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(1994)
J. Chem. Soc., Perkin Trans. 1
, pp. 277
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Ando, K.1
Yasuda, K.2
Tomioka, K.3
Koga, K.4
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32
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0343825926
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Some stereoselective reactions on the basis of the stereocontrol induced by the 1,3-allylic strain have been reported: a) Tomioka, K; Kawasaki, H.; Yasuda, K.; Koga, K. Tetrahedron Lett. 1986, 27, 3247.
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(1986)
Tetrahedron Lett.
, vol.27
, pp. 3247
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Tomioka, K.1
Kawasaki, H.2
Yasuda, K.3
Koga, K.4
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33
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0000274179
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b) Tomioka, K.; Kawasaki, H.; Yasuda, K.; Koga, K. J. Am. Chem. Soc. 1988, 110, 3597.
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(1988)
J. Am. Chem. Soc.
, vol.110
, pp. 3597
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Tomioka, K.1
Kawasaki, H.2
Yasuda, K.3
Koga, K.4
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34
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0029801091
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c) Moritani, Y.; Fukushima, T.; Ukita, T.; Miyagishima, T.; Ohmizu, H.; Iwasaki, T. J. Org. Chem. 1996, 61, 6922.
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(1996)
J. Org. Chem.
, vol.61
, pp. 6922
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Moritani, Y.1
Fukushima, T.2
Ukita, T.3
Miyagishima, T.4
Ohmizu, H.5
Iwasaki, T.6
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35
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0028270864
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The diastereoselective Michael addition reaction of nitromethyl anion and the lithium enolate to the ester 2 have been reported. In the case of nitromethyl anion, the selectivity was elucidated by the stereocontrol based on the 1,3-allylic strain. The present reaction is the first example of the diastereoselective Michael addition of an acyl anion equivalent to 2: a) Patrocinio, V. L.; Costa, P. R. R.; Correia, C. R. D. Synthesis 1994, 474.
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(1994)
Synthesis
, pp. 474
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Patrocinio, V.L.1
Costa, P.R.R.2
Correia, C.R.D.3
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36
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0027197163
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b) Nagaoka, H.; Shibuya, K.; Kobayashi, K.; Miura, I.; Muramatu, M.; Yamada, Y. Tetrahedron Lett. 1993, 34, 4039.
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(1993)
Tetrahedron Lett.
, vol.34
, pp. 4039
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Nagaoka, H.1
Shibuya, K.2
Kobayashi, K.3
Miura, I.4
Muramatu, M.5
Yamada, Y.6
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37
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0009406158
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The stereochemical outcome could be elucidated by using either s-cis and s-trans conformation of 2 and 10. Houk and co-workers have reported that s-cis conformation is slightly preferred to s-trans one in the transition state of the Michael addition reaction of a lithium amide to methyl crotonate. According to their result, the transition structures in Fig. 1 and Fig. 2 were shown utilizing the s-cis conformation: a) Rudolf, K.; Hawkins, J. M.; Loncharich, R. J.; Houk, K. N. J. Org. Chem. 1988, 53, 3879.
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(1988)
J. Org. Chem.
, vol.53
, pp. 3879
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Rudolf, K.1
Hawkins, J.M.2
Loncharich, R.J.3
Houk, K.N.4
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38
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33845283322
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b) Loncharich, R. J.; Schwartz, T. R.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 14.
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(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 14
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Loncharich, R.J.1
Schwartz, T.R.2
Houk, K.N.3
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39
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84889554050
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note
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The Michael addition of the corresponding dithiane compound to 2 was examined under the similar reaction conditions, however the diastereoselectivity was only 56% de. The rather smaller bulkiness of the 1,3-dithiane compound would brought about the low diastereoselectivity even in the presence of HMPA. (formula presented)
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40
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84889553150
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note
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1H NMR. The mixture was subjected to the next reaction without separation because both isomers were convertible into (+)-fargesin. Crystal data for 16a has been deposited at the Cambridge Crystallographic Data Centre. (formula presented)
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41
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84889528309
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note
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8h The optical purity of synthesized 6 was determined to be over 99% ee by HPLC. Theoretically, obtained 6 was 93% ee, but removal of the enantiomer would be achieved in the crystallization step of tetraol 20.
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42
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0026647113
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Review on synthesis of podophyllotoxin and related compounds: Ward, R. S. Synthesis 1992, 719.
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(1992)
Synthesis
, pp. 719
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Ward, R.S.1
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43
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0019951393
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and references cited therein
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Yalowich, J. D.; Fry, D. W.; Goldman, T. D. Cancer Res. 1982, 42, 3648 and references cited therein.
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(1982)
Cancer Res.
, vol.42
, pp. 3648
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Yalowich, J.D.1
Fry, D.W.2
Goldman, T.D.3
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45
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0000634229
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Fétizon, M.; Golfier, M.; Louis, J-M. Tetrahedron 1975, 31, 171.
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(1975)
Tetrahedron
, vol.31
, pp. 171
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Fétizon, M.1
Golfier, M.2
Louis, J.-M.3
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46
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84889558753
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note
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Oxidation of diol 22 was proceeded stereoselectively and no stereoisomer was obtained.
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47
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84889543624
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note
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In order to clarify whether racemization took place or not in the transformation of 21 to 23, 21 a and 21b were isolated and independently subjected to the transformation under the same reaction conditions. As a result, 21a and 21b were converted into 23a and 23b respectively without contamination of the isomer. (formula presented)
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48
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33747849809
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Gensler, W. J.; Johnson, F.; Sloan, A. D. B. J. Am. Chem. Soc. 1960, 82, 6074.
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(1960)
J. Am. Chem. Soc.
, vol.82
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Gensler, W.J.1
Johnson, F.2
Sloan, A.D.B.3
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