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d) Avrainvillamide was isolated independently from a soil sample collected in Venezuela and named CJ-17,665: Y. Sugie, H. Hirai, T. Inagaki, M. Ishiguro, Y. Kim, Y. Kojima, T. Sakakibara, A. Sakemi, Y. Suzuki, L. Brennan, J. Duignan, L. H. Huang, J. Sutcliffe, N. Kojima, J. Antibiot. 2001, 54, 911-916.
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For studies towards the total synthesis of the stephacidins or avrainvillamide, see: A. G. Myers, S. B. Herzon, J. Am. Chem. Soc. 2003, 125, 12080-12081;
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While this manuscript was under review, beautiful total syntheses of (-)-avrainvillamide and (+)-stephacidin B were reported: S. B. Herzon, A. G. Myers, J. Am. Chem. Soc. 2005, 127, 5342-5344.
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Proline 6 was synthesized by hydroboration, oxidation, esterification, and deprotection of the corresponding Cbz-protected enantiopure allylated proline, see: D. Seebach, M. Boes, R. Naef, W. B. Schweizer, J. Am. Chem. Soc. 1983, 105, 5390-5398;
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J. Fuchser, PhD Thesis, University of Göttingen, 1995.
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Fuchser, J.1
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Model 12 had identical spectral properties to those reported, see: R. M. Williams, T. Glinka, E. Kwast, H. Coffman, J. K. Stille, J. Am. Chem. Soc. 1990, 112, 808-821.
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25
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21244445673
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note
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Detailed experimental procedures and copies of all spectral data for 15, (+)-1, (+)-3, and (-)-2 are available in the Supporting Information.
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