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For a review of the chemistry and biology of immunosuppressive natural products, see: Mann, J. Nat. Prod. Rep. 2001, 18, 417.
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For related studies from the Evans group, see: a
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For related studies from the Evans group, see: (a) Evans, D. A.; Coleman, P. J.; Côté, B. J. Org. Chem. 1997, 62, 788.
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0342905533
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De Camp Schuda, A.1
Mazzocchi, P.H.2
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Morgan, T.4
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13
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Hon, Y.-S.1
Lu, L.2
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Lin, S.-W.4
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Kolb, H.C.1
VanNieuwenhze, M.S.2
Sharpless, K.B.3
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16
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62149125944
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See the Supporting Information for details
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See the Supporting Information for details.
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17
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0030828306
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(a) Ireland, R. E.; Liu, J.; Roper, T. D. Tetrahedron 1997, 53, 13221.
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Ireland, R.E.1
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18
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22744456562
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Trieselmann, T.7
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19
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0030810476
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Myers, A.G.1
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Gleason, J.L.6
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20
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0000504848
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(a) Evans, D. A.; Bilodeau, M. T.; Somers, T. C.; Clardy, J.; Cherry, D.; Kato, Y. J. Org. Chem. 1991, 56, 5750.
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Evans, D.A.1
Bilodeau, M.T.2
Somers, T.C.3
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Kato, Y.6
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21
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0037070544
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(b) Yokoshima, S.; Ueda, T.; Kobayashi, S.; Sato, A.; Kuboyama, T.; Tokuyama, H.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 2137.
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Yokoshima, S.1
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Kobayashi, S.3
Sato, A.4
Kuboyama, T.5
Tokuyama, H.6
Fukuyama, T.7
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22
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33845278140
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Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
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Evans, D.A.1
Chapman, K.T.2
Carreira, E.M.3
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23
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0001951357
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13C NMR analysis using Rychnovsky's method and (ii) treatment of 17 with DDQ to generate the corresponding 5,7-syn PMP acetal and NOE analysis. Rychnovsky, S.D.; Rogers, B. N.; Richardson, T. I. Acc. Chem. Res. 1998, 31, 9.
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13C NMR analysis using Rychnovsky's method and (ii) treatment of 17 with DDQ to generate the corresponding 5,7-syn PMP acetal and NOE analysis. Rychnovsky, S.D.; Rogers, B. N.; Richardson, T. I. Acc. Chem. Res. 1998, 31, 9.
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24
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39349099300
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We thank Dr. Rob Paton for carrying out transition state calculations for R1, Me and R2, E-CH=CHMe, where TS-I leading to adduct 21 was preferred. Paton, R. S, Goodman, J. M. J. Org. Chem. 2008, 73, 1253
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2 = (E)-CH=CHMe, where TS-I leading to adduct 21 was preferred. Paton, R. S.; Goodman, J. M. J. Org. Chem. 2008, 73, 1253.
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25
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2142858450
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The configuration was determined by use of the advanced Mosher method: Ohtani, I.; Kasumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
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The configuration was determined by use of the advanced Mosher method: Ohtani, I.; Kasumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
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26
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84987464056
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The use of an indicator (Sudan red 7B) was crucial to prevent oxidation of the PMB ethers. Veysoglu, T.; Mitscher, L. A.; Swayze, J. K. Synthesis 1980, 807.
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The use of an indicator (Sudan red 7B) was crucial to prevent oxidation of the PMB ethers. Veysoglu, T.; Mitscher, L. A.; Swayze, J. K. Synthesis 1980, 807.
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27
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62149139428
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The spectroscopic data of 2 matched that of material prepared via the route described in Scheme 4.
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The spectroscopic data of 2 matched that of material prepared via the route described in Scheme 4.
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