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For attempts at constructing the bicyclo[5.3.0]decenone skeleton via the intramolecular PKR of enynes, see: (a) Wender, P. A.; McDonald, F. E. Tetrahedron Lett. 1990, 31, 3691-3694.
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For construction of seven and larger-membered rings via PKR of enynes with an aromatic ring as a template, see: (a) Pérez-Serrano, L.; Casarrubios, L.; Domínguez, G.; Pérez-Castells, J. Chem. Commun. 2001, 2602-2603.
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(a) Mukai, C.; Nomura, I.; Yamanishi, K.; Hanaoka, M. Org. Lett. 2002, 4, 1755-1758.
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21
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2-catalyzed PKR of allenynes, which involves three successful examples of the formation of the bicyclo[5.3.0]decadienone skeleton: Brummond, K. M.; Chen, H.; Fisher, K. D.; Kerekes, A. D.; Rickards, B.; Sill, P. C.; Geib, S. J. Org. Lett. 2002, 4, 1931-1934.
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Sill, P.C.6
Geib, S.7
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23
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0001457964
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For other examples of the formation of the bicyclo[5.3.0]decane skeleton via transition metal-catalyzed PKR of allenynes, see: (a) Shibata, T.; Koga, Y.; Narasaka, K. Bull. Chem. Soc. Jpn. 1995, 68, 911-919.
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2 was first used in PKR by Jenog and co-workers, see: (a) Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642-3644.
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For Rh(I)-catalyzed enyne cycloisomerization, see: Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490-6491.
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Cao, P.1
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For Rh(I)-catalyzed allenene cycloisomerization, see: (a) Makino, T.; Itoh, K. Tetrahedron Lett. 2003, 44, 6335-6338.
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Makino, T.1
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0037176294
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2-catalyzed construction of six-membered triene derivatives: (a) Brummond, K. M.; Chen, H.; Sill, P.; You, L. J. Am. Chem. Soc. 2002, 124, 15186-15187.
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Shibata, T.; Takesue, Y.; Kadowaki, S.; Takagi, K. Synlett 2003, 268-270.
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40
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0033949371
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For other examples of transition-metal-catalyzed allenyne cycloisomerizations, see: (a) Pagenkopf, B. L.; Belanger, D. B.; O'Mahony, D. J. R.; Livinghouse, T. Synthesis 2000, 1009-1019.
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(b) Oh, C. H.; Jung, S. H.; Rhim, C. Y. Tetrahedron Lett. 2001, 42, 8669-8671.
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0002089886
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(b) Kobayashi, T.; Koga, Y.; Narasaka, K. J. Organomet. Chem. 2001, 624, 73-87.
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Kobayashi, T.1
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Narasaka, K.3
-
44
-
-
33645598781
-
-
note
-
2 could be observed.
-
-
-
-
45
-
-
33645585743
-
-
note
-
2.
-
-
-
-
46
-
-
33645600136
-
-
note
-
2 under 20 atm of CO, 6e was obtained in 81% yield along with 7e in 15% yield.
-
-
-
-
50
-
-
33645599305
-
-
note
-
(E)-Stereochemistry of 15 was determined on the basis of NOE experiments. For instance, 3.4% enhancement of vinyl protons and 1.5% enhancement of methyl group were recorded when Ha of 15c was irradiated.
-
-
-
-
53
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49549140207
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(b) Claesson, A.; Tämnefors, I.; Olsson, L. I. Tetrahedron Lett. 1975, 16, 1509-1512.
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Tetrahedron Lett.
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Claesson, A.1
Tämnefors, I.2
Olsson, L.I.3
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54
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0007044848
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(c) Kim, H. J.; Jang, J. Y.; Chung, K. H.; Lee, J. H. Biosci. Biotechnol. Biochem. 1999, 63, 494-499.
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Biosci. Biotechnol. Biochem.
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Kim, H.J.1
Jang, J.Y.2
Chung, K.H.3
Lee, J.H.4
-
55
-
-
33645596745
-
-
note
-
2 could be used for transformation of 5a-c into 7a-c in slightly lower yield [7a (69%), 7b (66%), and 7c (44%)].
-
-
-
-
56
-
-
33645589655
-
-
note
-
Compounds 7d (6%), 7e (31%), and 7f (48%) were obtained with recovery of the starting materials 5d (72%), 5e (51%), and 5f (36%), respectively.
-
-
-
-
57
-
-
33645583002
-
-
note
-
2 was found not to be a suitable catalyst for transformation of 10 into 12 [12a (30%), 12b (13%), and 12c (16%)].
-
-
-
-
58
-
-
33645589130
-
-
note
-
1H NMR spectra with those of carbon congeners.
-
-
-
-
59
-
-
33645584694
-
-
note
-
For example, an NOE experiment of 35b showed 6.1% enhancement of methyl group upon irradiation of vinyl proton, while 5.6% enhancement between methyl group and vinyl proton of 35c was observed.
-
-
-
-
60
-
-
33645593846
-
-
note
-
Data for crystallographic analysis of 35c was described in the Supporting Information.
-
-
-
-
63
-
-
0001261240
-
-
and references therein
-
(c) Dolbier, W. R., Jr.; Koroniak, H.; Houk, K. N.; Sheu, C. Acc. Chem. Res. 1996, 29, 471-477 and references therein.
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(1996)
Acc. Chem. Res.
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, pp. 471-477
-
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Dolbier Jr., W.R.1
Koroniak, H.2
Houk, K.N.3
Sheu, C.4
-
64
-
-
33645584058
-
-
note
-
1H NMR.
-
-
-
-
65
-
-
33645585474
-
-
note
-
Compounds 15c (10%) and 35c (42%) were isolated after refluxing a solution of 15c in xylene for 9 h.
-
-
-
-
66
-
-
33645588325
-
-
note
-
Compounds 36 were prepared by the standard procedure described in this paper; see the Supporting Information.
-
-
-
-
67
-
-
33645589395
-
-
note
-
Compounds 12d,e were exposed to xylene refluxing conditions leading to an intractable mixture.
-
-
-
-
68
-
-
33645593307
-
-
note
-
b bond could not be detected.
-
-
-
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