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For recent reviews on marine natural products, see: (a) Blunt J.W., Copp B.R., Munro M.H.G., Northcote P.T., Prinsep M.R. Nat. Prod. Rep. 20:2003;1 (b) Faulkner D.J. Nat. Prod. Rep. 19:2002;1 (c) Faulkner D.J. Nat. Prod. Rep. 18:2001;1 (d) Newman D.J., Cragg G.M., Snader K.M. Nat. Prod. Rep. 17:2000;215.
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For reviews on marine macrolide synthesis, see: (a) Norcross R.D., Paterson I. Chem. Rev. 95:1995;2041 (b) Yeung K.-S., Paterson I. Angew. Chem. Int. Ed. 41:2002;4632.
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For completed total syntheses of leucascandrolide A, see: (a) Hornberger K.R., Hamblett C.L., Leighton J.L. J. Am. Chem. Soc. 122:2000;12894 (b) Fettes A., Carreira E.M. Angew. Chem. Int. Ed. 41:2002;4098 (c) Wang Y., Janjic J., Kozmin S.A. J. Am. Chem. Soc. 124:2002;13670.
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85047700139
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For completed total syntheses of leucascandrolide A, see: (a) Hornberger K.R., Hamblett C.L., Leighton J.L. J. Am. Chem. Soc. 122:2000;12894 (b) Fettes A., Carreira E.M. Angew. Chem. Int. Ed. 41:2002;4098 (c) Wang Y., Janjic J., Kozmin S.A. J. Am. Chem. Soc. 124:2002;13670.
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Carreira, E.M.2
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0037146080
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For completed total syntheses of leucascandrolide A, see: (a)
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For completed total syntheses of leucascandrolide A, see: (a) Hornberger K.R., Hamblett C.L., Leighton J.L. J. Am. Chem. Soc. 122:2000;12894 (b) Fettes A., Carreira E.M. Angew. Chem. Int. Ed. 41:2002;4098 (c) Wang Y., Janjic J., Kozmin S.A. J. Am. Chem. Soc. 124:2002;13670.
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Wang, Y.1
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For formal syntheses of leucascandrolide A based on Ref. 6a, see: (a) Kopecky D.J., Rychnovsky S.D. J. Am. Chem. Soc. 123:2001;8420 (b) Wipf P., Reeves J.T. Chem. Commun. 2002;2066.
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0036401436
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For formal syntheses of leucascandrolide A based on Ref. 6a, see: (a)
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For formal syntheses of leucascandrolide A based on Ref. 6a, see: (a) Kopecky D.J., Rychnovsky S.D. J. Am. Chem. Soc. 123:2001;8420 (b) Wipf P., Reeves J.T. Chem. Commun. 2002;2066.
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Reeves, J.T.2
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For the synthesis of various leucascandrolide fragments, see: (a) Crimmins M.T., Carroll C.A., King B.W. Org. Lett. 2:2000;597 (b) Wipf P., Uto Y. J. Org. Chem. 65:2000;1037 (c) Wipf P., Graham T.H. J. Org. Chem. 66:2001;3242 (d) Dakin L.A., Langille N.F., Panek J.S. J. Org. Chem. 67:2002;6812 (e) Kozmin S.A. Org. Lett. 3:2001;755.
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0034712229
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For the synthesis of various leucascandrolide fragments, see: (a) Crimmins M.T., Carroll C.A., King B.W. Org. Lett. 2:2000;597 (b) Wipf P., Uto Y. J. Org. Chem. 65:2000;1037 (c) Wipf P., Graham T.H. J. Org. Chem. 66:2001;3242 (d) Dakin L.A., Langille N.F., Panek J.S. J. Org. Chem. 67:2002;6812 (e) Kozmin S.A. Org. Lett. 3:2001;755.
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For the synthesis of various leucascandrolide fragments, see: (a) Crimmins M.T., Carroll C.A., King B.W. Org. Lett. 2:2000;597 (b) Wipf P., Uto Y. J. Org. Chem. 65:2000;1037 (c) Wipf P., Graham T.H. J. Org. Chem. 66:2001;3242 (d) Dakin L.A., Langille N.F., Panek J.S. J. Org. Chem. 67:2002;6812 (e) Kozmin S.A. Org. Lett. 3:2001;755.
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For the synthesis of various leucascandrolide fragments, see: (a) Crimmins M.T., Carroll C.A., King B.W. Org. Lett. 2:2000;597 (b) Wipf P., Uto Y. J. Org. Chem. 65:2000;1037 (c) Wipf P., Graham T.H. J. Org. Chem. 66:2001;3242 (d) Dakin L.A., Langille N.F., Panek J.S. J. Org. Chem. 67:2002;6812 (e) Kozmin S.A. Org. Lett. 3:2001;755.
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For the synthesis of various leucascandrolide fragments, see: (a)
-
For the synthesis of various leucascandrolide fragments, see: (a) Crimmins M.T., Carroll C.A., King B.W. Org. Lett. 2:2000;597 (b) Wipf P., Uto Y. J. Org. Chem. 65:2000;1037 (c) Wipf P., Graham T.H. J. Org. Chem. 66:2001;3242 (d) Dakin L.A., Langille N.F., Panek J.S. J. Org. Chem. 67:2002;6812 (e) Kozmin S.A. Org. Lett. 3:2001;755.
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Kozmin, S.A.1
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24
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85031142797
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The enone was prepared from 3-buten-1-ol in 4 steps as described in Ref. 5
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The enone was prepared from 3-buten-1-ol in 4 steps as described in Ref. 5.
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26
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0034684178
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This homologation sequence was adapted from Evans and co-workers:
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This homologation sequence was adapted from Evans and co-workers: Evans D.A., Fitch D.M., Smith T.E., Cee V.J. J. Am. Chem. Soc. 122:2000;10033.
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0001790298
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For a review of asymmetric boron aldol reactions, see:
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0037213016
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Additional examples of this TEMPO-based methodology for selective δ-lactone formation have recently been reported by the Forsyth group, see:
-
Additional examples of this TEMPO-based methodology for selective δ-lactone formation have recently been reported by the Forsyth group, see: Hansen T.M., Florence G.J., Lugo-Mas P., Chen J., Abrams J.N., Forsyth C.J. Tetrahedron Lett. 44:2003;57.
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Forsyth, C.J.6
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33
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85031144617
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Silyl enol ether 6 was prepared from isovaleraldehyde as described in Ref. 5
-
Silyl enol ether 6 was prepared from isovaleraldehyde as described in Ref. 5.
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39
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84986437005
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Attempts to rationalise this outcome via molecular modelling of
-
Attempts to rationalise this outcome via molecular modelling of 33 using the MM2 force field in MacroModel have, as yet, proved inconclusive Mohamadi F., Richards N.G.J., Guida W.C., Liskamp R., Lipton M., Caufield C., Chang G., Hendrickson T., Still W.C. J. Comput. Chem. 11:1990;440.
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Caufield, C.6
Chang, G.7
Hendrickson, T.8
Still, W.C.9
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44
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85031142994
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For copies of NMR spectra, see the supporting information for Ref. 5
-
For copies of NMR spectra, see the supporting information for Ref. 5.
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