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Erickson, K.L.1
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(a) For a review of construction of medium-ring ethers, see: Elliott. M. C. Contemp. Org. Synth. 1994. 1, 457.
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Elliott, M.C.1
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0012187728
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Synthesis of marine natural products containing polycyclic ethers
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(b) Hirama, M.; Rainder, J. D.; Eds. Synthesis of marine natural products containing polycyclic ethers. Tetrahedron Symposium in Print No. 90 2002, 58, 1779-2040.
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Hirama, M.1
Rainder, J.D.2
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5
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0033574384
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(+)-obtusenyne
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(c) Fujiwara, K.; Awakura, D.; Tsunashima, M.; Nakamura, A.; Honma, T.; Murai, A. (+)-obtusenyne. J. Org. Chem. 1999, 64, 2616.
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6
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0029006233
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(d) For representative examples of total synthesis of (+)-laurencin, see: Bratz, M.; Bullock, W. H.; Overman, L. E.; Takemoto, T. J. Am. Chem. Soc. 1995, 117, 5958.
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(e) Burton, J. W.; Clark, J. S.; Derrer, S.; Stork, T. C.; Bendall, J. G.; Holmes, A. B. J. Am. Chem. Soc. 1997, 119, 7483.
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0000638917
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(a) Kinnel, R. B.; Dieter, R. K.; Meinwald, J.; Engen, D. V.; Clardy, J. Eisner, T.; Stallard, M. O.; Fenical, W. Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 3576.
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(b) Fenical, W.; Sleeper, H. L.; Paul, V. J.; Stallard, M. O.; Sun, H. H. Pure Appl. Chem. 1979, 51, 1865.
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13
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0012188051
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note
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The parent 2,3,4,9-tetrahydrooxonin ring is unknown.
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15
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0012183077
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note
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L-(S)-Malic acid was purchased from Aldrich and was shown to be of 99% ee by CSP-GLC analysis.
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16
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0012113481
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note
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All new compounds have been fully characterized, and all yields correspond to isolated, analytically pure materials. For detailed experimental procedures, see Supporting Information.
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17
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33845550948
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To the best of our knowledge, the ring opening of a 1,3-dioxolanone with bis(trimethylsilyl)acetylene is unprecedented. Ring opening of acetal templates with silylacetylenic compounds promoted by Lewis acid have been reported, see: (a) Johnson, W. S.; Elliott, R.; Elliott, J. D. J. Am. Chem. Soc. 1983, 105, 2904.
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Johnson, W.S.1
Elliott, R.2
Elliott, J.D.3
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18
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33845374196
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(b) Yamamoto, Y., Nishii, S.; Yamada, J.-i. J. Am. Chem. Soc. 1986, 108, 7116.
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Yamamoto, Y.1
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Yamada, J.-I.3
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21
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0012183078
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note
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8), whose full stereostructure was confirmed by single-crystal X-ray diffraction. The crystallographic coordinates of the cobalt complex have been deposited with the Cambridge Crystallographic Data Centre; deposition no. CCDC-195245.
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22
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84989539773
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Nishikawa, T.; Shibuya, S.; Hosokawa, S.; Isobe, M. Synlett 1994, 485.
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Synlett
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Nishikawa, T.1
Shibuya, S.2
Hosokawa, S.3
Isobe, M.4
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23
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0024819137
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For modified procedures, see: (a) Nicolaou, K. C.; Marron, B. E.; Veale, C. A.; Webber, S. E.; Serhan, C. N. J. Org. Chem. 1989, 54, 5527.
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Nicolaou, K.C.1
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Serhan, C.N.5
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24
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0035477040
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Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2001, 40, 3667.
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Chavez, D.E.1
Jacobsen, E.N.2
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25
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0028327029
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For a modified procedure, see: Nemoto, H.; Nagamochi, M.; Ishibashi, H.; Fukumoto, K. J. Org. Chem. 1994, 59, 74.
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Nemoto, H.1
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Fukumoto, K.4
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27
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0001343097
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2O, see: (a) Danishefsky, S. J.; Deninno, M. P.; Phillips, G. B.; Zelle, R. E. Tetrahedron 1986, 42, 2809.
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Danishefsky, S.J.1
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Phillips, G.B.3
Zelle, R.E.4
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28
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0001057466
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For addition of allyltributylstannes to α-alkoxy aldehydes, see: Keck, G. E.; Boden, E. P. Tetrahedron Lett. 1984, 25, 265.
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Keck, G.E.1
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0344934245
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Brown, H. C.; Bhat, K. S.: Randad, R. S. J. Org. Chem. 1989, 54, 1570.
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Brown, H.C.1
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31
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33751392358
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Schrock's molybdenum complex is commercially available (Strem) or can be prepared according to the reported procedure with consistent purity and reactivity, see: (a) Fox, H. H.; Yap, K. B.; Robbins, J.; Cai, S.; Schrock, R. R. Inorg. Chem. 1992, 31, 2287.
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Fox, H.H.1
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Schrock, R.R.5
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0001077422
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(b) Schrock, R. R.: Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875.
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Schrock, R.R.1
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33
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0000334943
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(c) Oskam, J. H.; Fox, H. H.; Yap, K. B.; McConville, D. H.; O'Dell, R.; Lichtenstein, B. J.; Schrock, R. R. J. Organomet. Chem. 1993, 459, 185.
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(d) Fox, H. H.; Lee, J.-K.; Park, L. Y.; Schrock, R. R. Organometallics 1993, 12, 759.
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46149140781
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Horita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y.; Yonemitsu, O. Tetrahedron 1986, 42, 3021.
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0001539666
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(b) See also Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568.
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