-
1
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34247169509
-
-
Very recent reviews: (a) Kobayashi, J.; Kubota, T. J. Nat. Prod. 2007, 70, 451.
-
Very recent reviews: (a) Kobayashi, J.; Kubota, T. J. Nat. Prod. 2007, 70, 451.
-
-
-
-
3
-
-
0242298257
-
-
amphi K C1-C5 chiral blocks
-
(a) Mas, G.; González, L; Vilarrasa, J. Tetrahedron Lett. 2003, 44, 8805 (amphi K C1-C5 chiral blocks).
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(2003)
Tetrahedron Lett
, vol.44
, pp. 8805
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-
Mas, G.1
González, L.2
Vilarrasa, J.3
-
4
-
-
25444476745
-
-
amphi K C9-C22 fragment
-
(b) Andreou, T.; Costa, A. M.; Esteban, L.; González, L.; Mas, G.; Vilarrasa, J. Org. Lett. 2005, 7, 4083 (amphi K C9-C22 fragment).
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(2005)
Org. Lett
, vol.7
, pp. 4083
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Andreou, T.1
Costa, A.M.2
Esteban, L.3
González, L.4
Mas, G.5
Vilarrasa, J.6
-
6
-
-
33947593955
-
-
amphi X/Y C12-C21 segments
-
(d) Rodríguez-Escrich, C.; Olivella, A.; Urpí, F.; Vilarrasa, J. Org. Lett. 2007, 9, 989 (amphi X/Y C12-C21 segments).
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Org. Lett
, vol.9
, pp. 989
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Rodríguez-Escrich, C.1
Olivella, A.2
Urpí, F.3
Vilarrasa, J.4
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7
-
-
38349148440
-
-
amphi E C1-C5 chiroblocks
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(e) Esteban, J.; Costa, A. M.; Gómez, A.; Vilarrasa, J. Org. Lett. 2008, 10, 65 (amphi E C1-C5 chiroblocks).
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(2008)
Org. Lett
, vol.10
, pp. 65
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Esteban, J.1
Costa, A.M.2
Gómez, A.3
Vilarrasa, J.4
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8
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-
60949104428
-
-
Ph.D. Thesis in process
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(f) Esteban, J. Ph.D. Thesis in process (2005-2008).
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(2005)
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Esteban, J.1
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9
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0025310709
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(a) Kobayashi, J.; Ishibashi, M.; Murayama, T.; Takamatsu, M; Iwamura, M.; Ohizumi, Y.; Sasaki, T. J. Org. Chem. 1990, 55, 3421.
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(1990)
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Kobayashi, J.1
Ishibashi, M.2
Murayama, T.3
Takamatsu, M.4
Iwamura, M.5
Ohizumi, Y.6
Sasaki, T.7
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10
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0037040665
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-
(b) Kubota, T.; Tsuda, M.; Kobayashi, J. J. Org. Chem. 2002, 67, 1651.
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(2002)
J. Org. Chem
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, pp. 1651
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Kubota, T.1
Tsuda, M.2
Kobayashi, J.3
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11
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-
33845491696
-
-
Total syntheses: (a) Kim, C. H.; An, H. J.; Shin, W. K.; Yu, W.; Woo, S. K.; Jung, S. K.; Lee, E. Angew. Chem., Int. Ed. 2006, 45, 8019.
-
Total syntheses: (a) Kim, C. H.; An, H. J.; Shin, W. K.; Yu, W.; Woo, S. K.; Jung, S. K.; Lee, E. Angew. Chem., Int. Ed. 2006, 45, 8019.
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-
-
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13
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33846594323
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For diastereomers of amphidinolide E, see: c
-
For diastereomers of amphidinolide E, see: (c) Va, P.; Roush, W. R. Org. Lett. 2007, 9, 307.
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(2007)
Org. Lett
, vol.9
, pp. 307
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Va, P.1
Roush, W.R.2
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15
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-
28244447487
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-
C6-C21, For syntheses of segments, see: a
-
For syntheses of segments, see: (a) Marshall, J. A.; Schaaf, G.; Nolting, A. Org. Lett. 2005, 7, 5331 (C6-C21).
-
(2005)
Org. Lett
, vol.7
, pp. 5331
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Marshall, J.A.1
Schaaf, G.2
Nolting, A.3
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16
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-
20544466457
-
-
C6-C21
-
(b) Heitzman, C. L.; Lambert, W. T.; Mertz, E.; Shotwell, J. B.; Tinsley. J. M.; Va, P.; Roush, W. R. Org. Lett. 2005, 7, 2405 (C6-C21).
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(2005)
Org. Lett
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Heitzman, C.L.1
Lambert, W.T.2
Mertz, E.3
Shotwell, J.B.4
Tinsley, J.M.5
Va, P.6
Roush, W.R.7
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17
-
-
4644232539
-
-
C12-C26
-
(c) Gurjar, M. K.; Mohapatra, S.; Phalgune, U. S.; Puranik, V. G.; Mohapatra, D. K. Tetrahedron Lett. 2004, 45, 7899 (C12-C26).
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(2004)
Tetrahedron Lett
, vol.45
, pp. 7899
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Gurjar, M.K.1
Mohapatra, S.2
Phalgune, U.S.3
Puranik, V.G.4
Mohapatra, D.K.5
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18
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60949089589
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-
Two approaches were envisaged by us at the very beginning of this project (ref 2f) for the key steps: (i) a macrolactonization under the mildest possible conditions (to avoid epimerization at C2) as the last step, after a J-K reaction (C9-C10 bond); (ii) a ring-closing metathesis under appropriate conditions in the final step, after the ester formation.
-
Two approaches were envisaged by us at the very beginning of this project (ref 2f) for the key steps: (i) a macrolactonization under the mildest possible conditions (to avoid epimerization at C2) as the last step, after a J-K reaction (C9-C10 bond); (ii) a ring-closing metathesis under appropriate conditions in the final step, after the ester formation.
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-
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19
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26844568935
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(a) Blakemore, P. R.; Cole, W. J.; Kocienski, P. J.; Morley, A. Synlett 1998, 26.
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(1998)
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Blakemore, P.R.1
Cole, W.J.2
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Morley, A.4
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21
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33847221746
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(c) Plesniak, K.; Zarecki, A.; Wicha, J. Top. Curr. Chem. 2007, 275, 163.
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Plesniak, K.1
Zarecki, A.2
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0026343021
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(b) Figadère, B.; Harmange, J.-C.; Laurens, A.; Cavé, A. Tetrahedron Lett. 1991, 32, 7539.
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Figadère, B.1
Harmange, J.-C.2
Laurens, A.3
Cavé, A.4
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24
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60949083631
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Also see ref 2b
-
(d) Also see ref 2b.
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26
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33947485488
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Schultz, H. S.; Freyermuth, H. B.; Bue, S. R. J. Org. Chem. 1963, 28, 1140.
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Schultz, H.S.1
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Bue, S.R.3
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27
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0029860478
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We prepared 3 from the Li enolate of N-propanoyl-4(S)-benzyloxazolidin-2-one and 2,3-dibromopropene. Its enantiomer is known: (a) Evans, D. A.; Kim, A. S. J. Am. Chem. Soc. 1996, 118, 11323.
-
We prepared 3 from the Li enolate of N-propanoyl-4(S)-benzyloxazolidin-2-one and 2,3-dibromopropene. Its enantiomer is known: (a) Evans, D. A.; Kim, A. S. J. Am. Chem. Soc. 1996, 118, 11323.
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28
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0023885132
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(b) Evans, D. A.; Bender, S. L.; Morris, J. J. Am. Chem. Soc. 1988, 110, 2506.
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Evans, D.A.1
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Morris, J.3
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29
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0034684178
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(a) Evans, D. A.; Fitch, D. M.; Smith, T. E.; Cee, V. J. J. Am. Chem. Soc. 2000, 122, 10033.
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Evans, D.A.1
Fitch, D.M.2
Smith, T.E.3
Cee, V.J.4
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30
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0037033212
-
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(b) Sivaramakrishnan, A.; Nadolski, G. T.; McAlexander, I. A.; Davidson, B. S. Tetrahedron Lett. 2002, 43, 213.
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Sivaramakrishnan, A.1
Nadolski, G.T.2
McAlexander, I.A.3
Davidson, B.S.4
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31
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4344635789
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(c) Williams, D. R.; Kiryanov, A. A.; Emde, U.; Clark, M. P.; Berliner, M. A.; Reeves, J. T. Proc. Nat. Acad. Sci. U.S.A. 2004, 101, 12058.
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Proc. Nat. Acad. Sci. U.S.A
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Williams, D.R.1
Kiryanov, A.A.2
Emde, U.3
Clark, M.P.4
Berliner, M.A.5
Reeves, J.T.6
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32
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30544453732
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(d) Kara, S.; Makino, K.; Hamada, Y. Tetrahedron Lett. 2006, 47, 1081.
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(2006)
Tetrahedron Lett
, vol.47
, pp. 1081
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Kara, S.1
Makino, K.2
Hamada, Y.3
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34
-
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33846473027
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(f) Lucas, B. S.; Gopaisamuthiram, V.; Burke, S. D. Angew. Chem., Int. Ed. 2007, 46, 769.
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(2007)
Angew. Chem., Int. Ed
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, pp. 769
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Lucas, B.S.1
Gopaisamuthiram, V.2
Burke, S.D.3
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36
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85047698843
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(b) Evans, D. A.; Rajapakse, H. A.; Chiu, A.; Stenkamp, D. Angew. Chem., Int. Ed. 2002, 41, 4573.
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(2002)
Angew. Chem., Int. Ed
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Evans, D.A.1
Rajapakse, H.A.2
Chiu, A.3
Stenkamp, D.4
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37
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0037182034
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(c) Compostella, F.; Franchini, L.; Panza, L.; Prosperi, D.; Ronchetti, F. Tetrahedron 2002, 58, 4425.
-
(2002)
Tetrahedron
, vol.58
, pp. 4425
-
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Compostella, F.1
Franchini, L.2
Panza, L.3
Prosperi, D.4
Ronchetti, F.5
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38
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33750972054
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(d) Vicente, J.; Huckins, J. R.; Rychnovsky, S. D. Angew. Chem., Int. Ed. 2006, 45, 7258.
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(2006)
Angew. Chem., Int. Ed
, vol.45
, pp. 7258
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Vicente, J.1
Huckins, J.R.2
Rychnovsky, S.D.3
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39
-
-
48249135701
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(e) Miyashita, K.; Tsunemi, T.; Hosokawa, T.; Ikejiri, M.; Imanishi, T. J. Org. Chem. 2008, 73, 5360.
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(2008)
J. Org. Chem
, vol.73
, pp. 5360
-
-
Miyashita, K.1
Tsunemi, T.2
Hosokawa, T.3
Ikejiri, M.4
Imanishi, T.5
-
40
-
-
33748632563
-
-
According to the Kishi rule (Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron 1984, 40, 2247), they should be 11a and 11b, respectively.
-
According to the Kishi rule (Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron 1984, 40, 2247), they should be 11a and 11b, respectively.
-
-
-
-
42
-
-
15044352051
-
-
2nd ed, Seller, M, Bolm, C, Eds, Wiley-VCH: Weinheim
-
(b) Kolb, H. C.; Sharpless, K. B. In Transition Metals for Organic Synthesis; 2nd ed.; Seller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 2004; Vol. 2, p 275.
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(2004)
Transition Metals for Organic Synthesis
, vol.2
, pp. 275
-
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Kolb, H.C.1
Sharpless, K.B.2
-
44
-
-
39049122216
-
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(d) Français, A.; Bedel, O.; Haudrechy, A. Tetrahedron 2008, 64, 2495.
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(2008)
Tetrahedron
, vol.64
, pp. 2495
-
-
Français, A.1
Bedel, O.2
Haudrechy, A.3
-
45
-
-
60949103573
-
-
See Supporting Information for the corresponding spectra. The largest HCCH coupling constant in the key moiety of 11b indicates an almost antiperiplanar arrangement of HIS and HIC, whereas the very small gauche 3J(H17H18) suggests a dihedral angle closer to 90° than to 60° (see the Newman projection through the C18-C17 bond in Figure 1, left, The value of 3J(H17COH) is also worth noting. The most relevant NOEs agree with these observations (with H16, H17, H18, Me29, and H 20 in the same, rear face, The depicted hydrogen bondings likely help to fix the conformation shown in Figure 1 left
-
20 in the same, rear face). The depicted hydrogen bondings likely help to fix the conformation shown in Figure 1 (left).
-
-
-
-
46
-
-
60949103080
-
-
29 may be accounted for by the main conformation depicted in Figure 1 (right); other possible minor rotamers (by counterclockwise 60° rotation of the C19-C18 bond and/or by clockwise rotation of the C18-C17 bond) cannot be ruled out.
-
29 may be accounted for by the main conformation depicted in Figure 1 (right); other possible minor rotamers (by counterclockwise 60° rotation of the C19-C18 bond and/or by clockwise rotation of the C18-C17 bond) cannot be ruled out.
-
-
-
-
47
-
-
60949092983
-
HSQC, and HMBC)
-
The structure of 13 was assigned on the basis of 2D-NMR spectra COSY
-
HH) are relevant,
-
HH) are relevant
-
-
-
48
-
-
60949100970
-
-
The oxygen atom of the oxolane ring may play a role in this selective cleavage. We would have preferred the reverse cleavage, to obtain mainly the C17-OPMB isomer, saving two steps, since later we need C 18-OH free (and, in principle, C 17-OH protected).
-
(b) The oxygen atom of the oxolane ring may play a role in this selective cleavage. We would have preferred the reverse cleavage, to obtain mainly the C17-OPMB isomer, saving two steps, since later we need C 18-OH free (and, in principle, C 17-OH protected).
-
-
-
-
49
-
-
0038034652
-
-
Several CM of this etheneboronate ester (2-ethenyl-4,4,5,5-tetramethyl-1, 3,2-dioxaborolane), with the Grubbs II reagent, have been reported: (a) Morrill, C.; Grubbs, R. H. J. Org. Chem. 2003, 68, 6031 (and refs 13 and 14 therein).
-
Several CM of this etheneboronate ester (2-ethenyl-4,4,5,5-tetramethyl-1, 3,2-dioxaborolane), with the Grubbs II reagent, have been reported: (a) Morrill, C.; Grubbs, R. H. J. Org. Chem. 2003, 68, 6031 (and refs 13 and 14 therein).
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-
-
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50
-
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13444259632
-
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(b) Funk, T. W.; Efskind, J.; Grubbs, R. H. Org. Lett. 2005, 7, 187.
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(2005)
Org. Lett
, vol.7
, pp. 187
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Funk, T.W.1
Efskind, J.2
Grubbs, R.H.3
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51
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4544235191
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For other alkenylboronates, see: c
-
For other alkenylboronates, see: (c) Morrill, C.; Funk, T. W.; Grubbs, R. H. Tetrahedron Lett. 2004, 45, 7733.
-
(2004)
Tetrahedron Lett
, vol.45
, pp. 7733
-
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Morrill, C.1
Funk, T.W.2
Grubbs, R.H.3
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52
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0034734340
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Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168.
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(2000)
J. Am. Chem. Soc
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Garber, S.B.1
Kingsbury, J.S.2
Gray, B.L.3
Hoveyda, A.H.4
-
53
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38749104743
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-
Very recent review of potassium organotrifluoroborates: Darses, S.; Genet, J.-P. Chem. Rev. 2008, 108, 288.
-
Very recent review of potassium organotrifluoroborates: Darses, S.; Genet, J.-P. Chem. Rev. 2008, 108, 288.
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-
-
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54
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18744380684
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3. See: (a) Molander, G. A.; Felix, L. A. J. Org. Chem. 2005, 70, 3950.
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3. See: (a) Molander, G. A.; Felix, L. A. J. Org. Chem. 2005, 70, 3950.
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-
-
-
55
-
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34547235970
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For an example in anhydrous THF, see: b
-
For an example in anhydrous THF, see: (b) Fürstner, A.; Larionov, O.; Flügge, S. Angew. Chem., Int. Ed. 2007, 46, 5545.
-
(2007)
Angew. Chem., Int. Ed
, vol.46
, pp. 5545
-
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Fürstner, A.1
Larionov, O.2
Flügge, S.3
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56
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21144447140
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For reviews, see: c
-
For reviews, see: (c) Molander, G. A.; Figueroa, R. Aldrichimica Acta 2005, 38, 49.
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(2005)
Aldrichimica Acta
, vol.38
, pp. 49
-
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Molander, G.A.1
Figueroa, R.2
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58
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60949085363
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2O (300 mol %) in DMF. Compare: (a) Gopalarathnarn, A.; Nelson, S. G. Org. Lett. 2006, 8, 7.
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2O (300 mol %) in DMF. Compare: (a) Gopalarathnarn, A.; Nelson, S. G. Org. Lett. 2006, 8, 7.
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-
-
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59
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34547467855
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(b) Fürstner, A.; Nevado, C.; Waser, M.; Tremblay, M.; Chevrier, C.; Teply, F.; Aissa, C.; Moulin, E.; Müller, O. J. Am. Chem. Soc. 2007, 129, 9150.
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(2007)
J. Am. Chem. Soc
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, pp. 9150
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Fürstner, A.1
Nevado, C.2
Waser, M.3
Tremblay, M.4
Chevrier, C.5
Teply, F.6
Aissa, C.7
Moulin, E.8
Müller, O.9
-
60
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51349111666
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Most recent review: Doucet, H. Eur. J. Org. Chem. 2008, 2013.
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(c) Most recent review: Doucet, H. Eur. J. Org. Chem. 2008, 2013.
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-
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61
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60949096260
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Oxidative removal (e.g., with DDQ) of PMP and PMB groups is counterindicated as conjugate dienes are too sensitive; for an overview, see: Wutts, P. G. M.; Greene, T. W. Protective Groups in Organic Synthesis, 4th ed.; Wiley: Hoboken, 2007, p 124.
-
Oxidative removal (e.g., with DDQ) of PMP and PMB groups is counterindicated as conjugate dienes are too sensitive; for an overview, see: Wutts, P. G. M.; Greene, T. W. Protective Groups in Organic Synthesis, 4th ed.; Wiley: Hoboken, 2007, p 124.
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-
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