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5
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0344081833
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Harris J.B. (Ed), Clarendon, Oxford
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Shimizu Y. In: Harris J.B. (Ed). Natural Toxins: Animal, Plant, and Microbial (1986), Clarendon, Oxford 123
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Shimizu, Y.1
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7
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Wang Z.-X., Tu Y., Frohn M., Zhang J.-R., and Shi Y. J. Am. Chem. Soc. 119 (1997) 11224
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Wang, Z.-X.1
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8
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0000443501
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Frohn M., Dalkiewicz M., Tu Y., Wang Z.-X., and Shi Y. J. Org. Chem. 63 (1998) 2948
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Frohn, M.1
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Shi, Y.5
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14
-
-
33845506576
-
-
The bond dissociation energy of the doubly allylic C-H bonds in 1,4-pentadiene is quite low; it has been measured at 68.5 kcal/mol. See:
-
The bond dissociation energy of the doubly allylic C-H bonds in 1,4-pentadiene is quite low; it has been measured at 68.5 kcal/mol. See:. McMahon T.B., and Kebarle P. J. Am. Chem. Soc. 96 (1974) 5940
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McMahon, T.B.1
Kebarle, P.2
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20
-
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67650275167
-
-
note
-
In Scheme 1, distal Me groups are shown in red and proximal in blue, for clarity.
-
-
-
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21
-
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67650278382
-
-
For examples of highly endo-regioselective intramolecular opening of distally Me-substituted epoxides under acidic conditions, see
-
For examples of highly endo-regioselective intramolecular opening of distally Me-substituted epoxides under acidic conditions, see:
-
-
-
-
22
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0141630583
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-
Bravo F., McDonald F.E., Neiwert W.A., Do B., and Hardcastle K.I. Org. Lett. 5 (2003) 2123
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Bravo, F.1
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Hardcastle, K.I.5
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26
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31444438062
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Morimoto Y., Nishikawa Y., Ueba C., and Tanaka T. Angew. Chem., Int. Ed. 45 (2006) 810
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Angew. Chem., Int. Ed.
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Morimoto, Y.1
Nishikawa, Y.2
Ueba, C.3
Tanaka, T.4
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27
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67650278566
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For a canonical example of highly exo-regioselective intramolecular opening of proximally Me-substituted epoxides under acidic conditions, see
-
For a canonical example of highly exo-regioselective intramolecular opening of proximally Me-substituted epoxides under acidic conditions, see:
-
-
-
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31
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0011177417
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Ewing J.C., Ferguson G.S., Moore D.W., Shultz F.W., and Thompson D.W. J. Org. Chem. 50 (1985) 2124
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Ewing, J.C.1
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32
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4444331088
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Kaneda K., Kawamoto F., Fujiwara Y., Imanaka T., and Teranishi S. Tetrahedron Lett. 12 (1974) 1067
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Kaneda, K.1
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Teranishi, S.5
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33
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0003007598
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Kaneda K., Uchiyama T., Fujiwara Y., Imanaka T., and Teranishi S. J. Org. Chem. 44 (1979) 55
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Kaneda, K.1
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Teranishi, S.5
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34
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67650275894
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-
A racemic synthesis of 4 was reported by Bowman and McDonald:
-
A racemic synthesis of 4 was reported by Bowman and McDonald:
-
-
-
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36
-
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67650271868
-
-
(+)-4, the enantiomer of 4, has been prepared by the Nakata group:
-
(+)-4, the enantiomer of 4, has been prepared by the Nakata group:
-
-
-
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37
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0034606975
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Matsuo G., Hinou H., Koshino H., Suenaga T., and Nakata T. Tetrahedron Lett. 41 (2000) 903
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(2000)
Tetrahedron Lett.
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Matsuo, G.1
Hinou, H.2
Koshino, H.3
Suenaga, T.4
Nakata, T.5
-
38
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0001032404
-
-
A previous asymmetric synthesis of 4 by the Jamison group is reported in Ref. 10a. We report a streamlined gram-scale synthesis of 4, requiring five steps from 2,3-dihydropyran, in Supplementary data to Ref. 14
-
Suzuki K., and Nakata T. Org. Lett. 4 (2002) 2739 A previous asymmetric synthesis of 4 by the Jamison group is reported in Ref. 10a. We report a streamlined gram-scale synthesis of 4, requiring five steps from 2,3-dihydropyran, in Supplementary data to Ref. 14
-
(2002)
Org. Lett.
, vol.4
, pp. 2739
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Suzuki, K.1
Nakata, T.2
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39
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67650277325
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Initial report
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Initial report:
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-
-
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41
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67650256647
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-
Successful carbometallation in the presence of free hydroxyl groups
-
Successful carbometallation in the presence of free hydroxyl groups:
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-
-
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43
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67650271864
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Recent review
-
Recent review:
-
-
-
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47
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67650275570
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For a general review of the 1,2-difunctionalization of alkynes via metallometalation, see
-
For a general review of the 1,2-difunctionalization of alkynes via metallometalation, see:
-
-
-
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49
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67650277327
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For a recent review of silylcupration, see
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For a recent review of silylcupration, see:
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-
-
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51
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67650278869
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For a recent review of stannylcupration, see
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For a recent review of stannylcupration, see:
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-
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53
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37049088684
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-
The conditions that effected a trace of the desired product were taken from:
-
The conditions that effected a trace of the desired product were taken from:. Barbero A., Cuadrado P., Flemin I., González A.M., Pulido F.J., and Rubio R. J. Chem. Soc., Perkin Trans. 1 (1993) 1657
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(1993)
J. Chem. Soc., Perkin Trans. 1
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Barbero, A.1
Cuadrado, P.2
Flemin, I.3
González, A.M.4
Pulido, F.J.5
Rubio, R.6
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54
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2942536806
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Nagamitsu T., Takano D., Fukuda T., Otoguro K., Kuwajima I., Harigaya Y., and Omura S. Org. Lett. 6 (2004) 1865
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Nagamitsu, T.1
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Harigaya, Y.6
Omura, S.7
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55
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67650271866
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For a few examples of the manifold potential electrophilic quenches and transmetalation possibilities open to alkenylaluminum and alkenylcopper species, including conjugated additions, transmetalation to Pd, and subsequent cross-coupling, see
-
For a few examples of the manifold potential electrophilic quenches and transmetalation possibilities open to alkenylaluminum and alkenylcopper species, including conjugated additions, transmetalation to Pd, and subsequent cross-coupling, see:
-
-
-
-
67
-
-
67650276586
-
-
note
-
3 was found to improve yield slightly. Remarkably, a trace of silyl ether cleavage was observed in the absence of this base, presumably due to a small quantity of HBr in solution.
-
-
-
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68
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67650278380
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For discussions of improving the stereoselectivity and reactivity of cross metatheses, see
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For discussions of improving the stereoselectivity and reactivity of cross metatheses, see:
-
-
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-
69
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0034639441
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Blackwell H.E., O'Leary D.J., Chatterjee A.K., Washenfelder R.A., Bussmann D.A., and Grubbs R.H. J. Am. Chem. Soc. 122 (2000) 58
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Blackwell, H.E.1
O'Leary, D.J.2
Chatterjee, A.K.3
Washenfelder, R.A.4
Bussmann, D.A.5
Grubbs, R.H.6
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71
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67650277326
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For a recent review, see
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For a recent review, see:
-
-
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73
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33646561851
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Patel J., Mujcinovic S., Jackson W.R., Robinson A.J., Serelis A.K., and Such C. Green Chem. 8 (2006) 450
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Green Chem.
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Patel, J.1
Mujcinovic, S.2
Jackson, W.R.3
Robinson, A.J.4
Serelis, A.K.5
Such, C.6
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79
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67650276927
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For an overview of the bulky, electron-rich biaryl phosphines developed by the Buchwald group, see
-
For an overview of the bulky, electron-rich biaryl phosphines developed by the Buchwald group, see:
-
-
-
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