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1
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0006722484
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0042496482
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3
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33750440080
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note
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The absolute configuration of antheliolide A has remained undetermined.
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-
-
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4
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0030928683
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Antheliolide A is related structurally to the xenicane family of marine natural products: Hooper, G. J.; Davies-Coleman, M. T.; Schleyer, M. J. Nat. Prod. 1997, 60, 889-893.
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Hooper, G.J.1
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5
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33750456774
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note
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The vinylic bromide 2 was prepared in 91% yield by reaction of prenylmagnesium bromide with 2-bromoallyl bromide in the presence of 10 mol % of CuCN in THF at -78 °C for 2 h.
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7
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33750474347
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note
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2Si-protected geraniol.
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9
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0018410663
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12
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0023838949
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Corey, E.J.1
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Houpis, I.N.5
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14
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0001362730
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15
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0345025244
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(e) Snider, B. B.; Hui, R. A. H. F.; Kulkarni, Y. S. J. Am. Chem. Soc. 1985, 107, 2194-2196.
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Snider, B.B.1
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17
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33750451843
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note
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This separation was accomplished in one pass using a 2 cm diameter OD-H column available from Chiral Technologies, Inc.
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19
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0032388369
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Hiroi, K.1
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24
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33750435808
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note
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This assignment is also consistent with a three-dimensional analysis of the structures 13 and 19 for an n → π* transition as the basis for optical rotation.
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25
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33947093052
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(a) Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611-3613.
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Pine, S.H.1
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Corey, E.J.1
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33644986503
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(b) Hong, B.-C.; Kim, S.; Kim, T.-S.; Corey, E. J. Tetrahedron Lett. 2006, 47, 2711-2715.
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Hong, B.-C.1
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0027997412
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Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639-666.
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Ley, S.V.1
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31
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0000352038
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(a) Davis, F. A.; Vishwakarma, L. C.; Billmers, J. G.; Finn, J. J. Org. Chem. 1984, 49, 3241-3243.
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Davis, F.A.1
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32
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33750471414
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note
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2S before product isolation in order to prevent further oxidation of the α-hydroxy lactone.
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33
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0342809552
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(a) Ogura, H.; Takahashi, H.; Itoh, T. J. Org. Chem. 1972, 37, 72-75.
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Ogura, H.1
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34
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33750465744
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note
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(b) 1-Lithiopropyne was generated by reaction of 1-bromo-1-propene with n-Buli in THF at -78 °C for 2 h.
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36
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33750434742
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note
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A sample of naturally occurring antheliolide A (ca. 200 μg) was obtained from Prof. Yoel Kashman, Tel Aviv University, who generously provided his remaining stock of natural 1 for this research.
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37
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33750451465
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note
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Details are provided in the Supporting Information.
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38
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0343940257
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