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4
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36849035784
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Christmann, M., Braese, S., Eds.; Wiley-VCH: Weinheim, and references therein
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For the synthesis of 1 and 3, see: (a) de Meijere, A.; Larionov, O. V. In Asymmetric Synthesis The Essentials; Christmann, M., Braese, S., Eds.; Wiley-VCH: Weinheim, 2007; pp 67-7.1 and references therein,
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De Meijere, A.1
Larionov, O.V.2
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(c) Larionov, O. V.; Kozhushkov, S. I.; Brandi, M.; de Meijere, A. Mendeleev Commun. 2003, 199-200.
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Larionov, O.V.1
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De Meijere, A.4
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29044443217
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(e) Bégis, G.; Sheppard, T. D.; Cladingboel, D. E.; Motherwell, W. B.; Tocher, D. A. Synthesis 2005, 3186-3188.
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Bégis, G.1
Sheppard, T.D.2
Cladingboel, D.E.3
Motherwell, W.B.4
Tocher, D.A.5
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15
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52949147839
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(f) Yoshida, K.; Yamaguchi, K.; Sone, T.; Unno Y.; Asai, A.; Yokosawa, H.; Matsuda, A.; Arisawa, M.; Shuto, S. Org. Lett. 2008, 10, 3571-3574.
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Yoshida, K.1
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Sone, T.3
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Asai, A.5
Yokosawa, H.6
Matsuda, A.7
Arisawa, M.8
Shuto, S.9
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16
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64549086299
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(a) Yoshida, K.; Yamaguchi, K.; Mizuno, A.; Unno, Y.; Asai, A.; Sone, T.; Yokosawa, H.; Matsuda, A.; Arisawa, M.; Shuto, S. Org. Biomol. Chem. 2009, 7, 1868-1877.
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Unno, Y.4
Asai, A.5
Sone, T.6
Yokosawa, H.7
Matsuda, A.8
Arisawa, M.9
Shuto, S.10
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17
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53449087088
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(b) Hasegawa, M.; Kinoshita, K.; Nishimura, C.; Matsumura, U.; Shionyu, M.; Ikeda, S.; Mizukami, T. Bio. Med. Chem. Lett. 2008, 18, 5668-5671.
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Nishimura, C.3
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Shionyu, M.5
Ikeda, S.6
Mizukami, T.7
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19
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5444246119
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For structural stereogenic elucidations of 1 and 2, see
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(b) Zlatopolskiy, B. D.; Loscha, K.; Alvermann, P.; Kozhushkov, S. I.; Nikolaev, S. V.; Zeeck, A.; de Meijere, A. Chem-Eur. J. 2004, 10, 4708-4717. For structural stereogenic elucidations of 1 and 2, see:
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Zlatopolskiy, B.D.1
Loscha, K.2
Alvermann, P.3
Kozhushkov, S.I.4
Nikolaev, S.V.5
Zeeck, A.6
De Meijere, A.7
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20
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15044338608
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(c) Kozhushkov, S. I.; Zlatopolskiy, B. D.; Brandi, M.; Alvermann, P.; Radzom, M.; Geers, B.; de Meijere, A.; Zeeck, A. Eur. J. Org. Chem. 2005, 854-863.
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Kozhushkov, S.I.1
Zlatopolskiy, B.D.2
Brandi, M.3
Alvermann, P.4
Radzom, M.5
Geers, B.6
De Meijere, A.7
Zeeck, A.8
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21
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18744406740
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(d) Remscheid, U. M.; Ziatopolskiy, B. D.; Griesinger, C.; Zeeck, A.; de Meijere, A. Chem.-Eur. J. 2005, .11, 2929-2945.
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Remscheid, U.M.1
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Griesinger, C.3
Zeeck, A.4
De Meijere, A.5
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22
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76849099112
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de Meijere et al. have reported an elegant synthesis of 4 using the separation of two diastereoisomers obtained from an asymmetric alkylation reaction on a racemic mixture of nitrocyclopropanes: ref 7b
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de Meijere et al. have reported an elegant synthesis of 4 using the separation of two diastereoisomers obtained from an asymmetric alkylation reaction on a racemic mixture of nitrocyclopropanes: ref 7b.
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23
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0032546133
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(a) Moriarty, R. M.; May, E. J.; Guo, L.; Prakash, O. Tetrahedron Lett. 1998, 39, 765-766.
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(b) Honma, M.; Takeda, H.; Takano, M.; Nakada, M. Synlett 2009, 1695-1712.
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Charette, A.B.1
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32
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0037163295
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For previously reported reaction on 5a, see: Snider, B. B.; Che, Q. Tetrahedron 2002, 58, 7821-7827.
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Tetrahedron
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Snider, B.B.1
Che, Q.2
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0001488391
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(a) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467-8468.
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33751554479
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(c) Roush, W. R.; Hoong, L. K.; Palmer, M. A. J.; Straub, J. A.; Palkowitz, A. D. J. Org. Chem. 1990, 55, 4117-4126.
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Sylvain, C.; Wagner, A.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 875-878.
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Sylvain, C.1
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37
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76849099696
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Erosion, of the ee (from 97 to 53% ee) for compound 9 was observed in the first unoptimized Mitsunobu reaction attempts
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Erosion, of the ee (from 97 to 53% ee) for compound 9 was observed in the first unoptimized Mitsunobu reaction attempts.
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38
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76849104288
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-NSuc. and -OTBS substituted diazoesters generated poor diastereoselectivities (3:1 and 1:1, respectively) along with moderate yields. Iodonium ylide cyclopropanation of 11 afforded 15a in 51% yield
-
-NSuc. and -OTBS substituted diazoesters generated poor diastereoselectivities (3:1 and 1:1, respectively) along with moderate yields. Iodonium ylide cyclopropanation of 11 afforded 15a in 51% yield.
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39
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76849113599
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See Supporting Information for NOESY experiment on the relative configurations of 18 and X-Ray details of 19
-
See Supporting Information for NOESY experiment on the relative configurations of 18 and X-Ray details of 19.
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40
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76849103908
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Ensuing steps to the oxidation of 19 using methylester derivatives afforded the corresponding deprotected acid along with cyclopropane opening by-products
-
Ensuing steps to the oxidation of 19 using methylester derivatives afforded the corresponding deprotected acid along with cyclopropane opening by-products.
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41
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76849111198
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See Supporting Information for NOESY experiment on the relative configuration of 22
-
See Supporting Information for NOESY experiment on the relative configuration of 22.
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42
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76849111537
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References 5b and 7b reported the synthesis of protected (AcP) and (NcP)Ala in 16% yield over 8 steps and 13% yield over 6 steps, respectively
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References 5b and 7b reported the synthesis of protected (AcP) and (NcP)Ala in 16% yield over 8 steps and 13% yield over 6 steps, respectively.
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