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2
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0021061569
-
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note
-
30 unsaturated hydrocarbon with the same carbon skeleton as 7,11-cyclobotryococca-5,12,26-triene may have previously been isolated. See: ref 1 and Requejo, A. G.; Quinn, J. G. Geochim. Cosmochim. Acta 1983, 47, 1075-1090
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Requejo, A.G.1
Quinn, J.G.2
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3
-
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70349443542
-
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For discussions concerning the biosynthesis of 1 see ref 1 and
-
For discussions concerning the biosynthesis of 1 see ref 1 and Pan, J.-J.; Bugni, T. S.; Poulter, C. D. J. Org. Chem. 2009, 74, 7562-7565
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4
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77953595484
-
-
For reviews on the asymmetric synthesis of all carbon quaternary stereocenters see
-
For reviews on the asymmetric synthesis of all carbon quaternary stereocenters see
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5
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0035905575
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Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591-4597
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33846112164
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Kambara, H.; Yamada, T.; Tsujioka, M.; Matsunaga, S.; Tanaka, R.; Ali, H. I.; Wiart, C.; Yusof, M.; Hassan, H.; Hanifah, A.; Fauzi, Z. M.; Mazlan, N. H.; Jay, M.; Kunishima, M.; Akaho, E. Chem. Biodiversity 2006, 3, 1301-1306
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9
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44349189891
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Powell, L. H.; Docherty, P. H.; Hulcoop, D. G.; Kemmitt, P. D.; Burton, J. W. Chem. Commun. 2008, 2559-2561
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Burton, J.W.5
-
10
-
-
77953606575
-
-
For reviews of the use of manganese(III) acetate in organic synthesis see
-
For reviews of the use of manganese(III) acetate in organic synthesis see
-
-
-
-
15
-
-
0035951928
-
-
Gross, A.; Borcherding, D. R.; Friedrich, D.; Sabol, J. S. Tetrahedron Lett. 2001, 42, 1631-1633
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Gross, A.1
Borcherding, D.R.2
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Sabol, J.S.4
-
16
-
-
77953597592
-
-
For the use of copper(II) triflate in conjunction with manganese(III) acetate, see
-
For the use of copper(II) triflate in conjunction with manganese(III) acetate, see
-
-
-
-
17
-
-
0035951920
-
-
Toyao, A.; Chikaoka, S.; Takeda, Y.; Tamura, O.; Muraoka, O.; Tanabe, G.; Ishibashi, H. Tetrahedron Lett. 2001, 42, 1729-1732
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Toyao, A.1
Chikaoka, S.2
Takeda, Y.3
Tamura, O.4
Muraoka, O.5
Tanabe, G.6
Ishibashi, H.7
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19
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2342505765
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Hulcoop, D. G.; Sheldrake, H. M.; Burton, J. W. Org. Biomol. Chem. 2004, 2, 965-967
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Hulcoop, D.G.1
Sheldrake, H.M.2
Burton, J.W.3
-
20
-
-
77953548495
-
-
For the synthesis of γ-lactones using (a) manganese(III) acetate and copper(II) acetate see
-
For the synthesis of γ-lactones using (a) manganese(III) acetate and copper(II) acetate see
-
-
-
-
22
-
-
0026769153
-
-
Cerium(IV) ammonium nitrate see
-
Cerium(IV) ammonium nitrate see: Baciocchi, E.; Paolobelli, A. B.; Ruzziconi, R. Tetrahedron 1992, 48, 4617-4622
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(1992)
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Baciocchi, E.1
Paolobelli, A.B.2
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0001414464
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Rudolf, K.; Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 3708-3710
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Spellmeyer, D.C.2
Houk, K.N.3
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25
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37049091940
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Freiberg, M.; Meyerstein, D. J. Chem. Soc., Faraday Trans. 1 1980, 76, 1825-1837
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26
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37049091938
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Freiberg, M.; Mulac, W. A.; Schmidt, K. H.; Meyerstein, D. J. Chem. Soc., Faraday Trans. 1 1980, 76, 1838-1848
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27
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72149130393
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Ed.; Wiley: New York
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Kochi, J.K.1
Kochi, J.K.2
-
28
-
-
77953575777
-
-
note
-
This reaction was conducted on ca. 1 g scale. On a smaller scale (ca. 300 mg), the yield can be as high as 90%.
-
-
-
-
30
-
-
0001022759
-
-
Petasis, N. A.; Lu, S. P.; Bzowej, E. I.; Fu, D. K.; Staszewski, J. P.; AkritopoulouZanze, I.; Patane, M. A.; Hu, Y. H. Pure Appl. Chem. 1996, 68, 667-670
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Akritopoulouzanze, I.6
Patane, M.A.7
Hu, Y.H.8
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31
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1842506625
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33947093052
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36
-
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77953574176
-
-
For a review on the Synthesis of highly substituted olefins see
-
For a review on the Synthesis of highly substituted olefins see
-
-
-
-
38
-
-
77953549508
-
-
For a recent example of difficulty encountered when using a Wittig reaction to form a trisubstituted olefin see
-
For a recent example of difficulty encountered when using a Wittig reaction to form a trisubstituted olefin see
-
-
-
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39
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69949155630
-
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40
-
-
77953589694
-
-
For a recent example of competitive hydrometallation of a terminal olefin in the presence of an internal acetylene see
-
For a recent example of competitive hydrometallation of a terminal olefin in the presence of an internal acetylene see
-
-
-
-
41
-
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33845269745
-
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Semmelhack, M. F.; Hooley, R. J.; Kraml, C. M. Org. Lett. 2006, 8, 5203-5206
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0010324359
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0000362838
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45
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0343869642
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-
47
-
-
77953563303
-
-
For recent examples in natural product synthesis see
-
For recent examples in natural product synthesis see
-
-
-
-
48
-
-
0001284819
-
-
Wender, P. A.; Jesudason, C. D.; Nakahira, H.; Tamura, N.; Tebbe, A. L.; Ueno, Y. J. Am. Chem. Soc. 1997, 119, 12976-12977
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Wender, P.A.1
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Nakahira, H.3
Tamura, N.4
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Ueno, Y.6
-
49
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36849070454
-
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Smith, A. B.; Basu, K.; Bosanac, T. J. Am. Chem. Soc. 2007, 129, 14872-14874
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50
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Smith, A. B.; Bosanac, T.; Basu, K. J. Am. Chem. Soc. 2009, 131, 2348-2358
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Basu, K.3
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53
-
-
77953582875
-
-
For a review on organocopper chemistry see
-
For a review on organocopper chemistry see
-
-
-
-
55
-
-
77953600137
-
-
This is the procedure described by Monte and Lindbeck
-
This is the procedure described by Monte and Lindbeck
-
-
-
-
57
-
-
77953598535
-
-
note
-
1H NMR of the coupled product 2 did not indicate the presence of any other alkene diastereomers.
-
-
-
-
59
-
-
1542504084
-
-
Muller, S.; Liepold, B.; Roth, G. J.; Bestmann, H. J. Synlett 1996, 521-522
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Muller, S.1
Liepold, B.2
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Bestmann, H.J.4
-
60
-
-
77953575461
-
-
We followed the procedure of Uguen and co-worker for the preparation of the allylic alcohol 22 from the acetylene 19
-
We followed the procedure of Uguen and co-worker for the preparation of the allylic alcohol 22 from the acetylene 19
-
-
-
-
61
-
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0030919674
-
-
Zoller, T.; Uguen, D.; DeCian, A.; Fischer, J.; Sable, S. Tetrahedron Lett. 1997, 38, 3409-3412
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(1997)
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Zoller, T.1
Uguen, D.2
Decian, A.3
Fischer, J.4
Sable, S.5
-
62
-
-
77953608320
-
-
note
-
The assignment of the structures 23 and 24 is only tentative as isolation of pure compounds was not possible. The formation of 23 and 24 may be due to the formation of isomeric allylic chlorides in the previous step.
-
-
-
-
63
-
-
77953565840
-
-
Further purification provided pure 1
-
Further purification provided pure 1.
-
-
-
-
64
-
-
77953579174
-
-
13C NMR resonance is quoted at δ = 25.79 ppm, whereas in the original spectra, and the spectra of the synthetic material, C-15 resonates at δ = 24.80 ppm
-
13C NMR resonance is quoted at δ = 25.79 ppm, whereas in the original spectra, and the spectra of the synthetic material, C-15 resonates at δ = 24.80 ppm.
-
-
-
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