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12 was synthesized in five steps from 2-hepten-1-ol: (a) Ti(O-i-Pr)4, L-DIPT, t-BuOOH (87%); (b) Me3Al (75%); (c) PhCH(OMe)2, CSA (74%); (d) DIBAL (95%); (e) IBX (83%). See the Supporting Information for details.
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12 was synthesized in five steps from 2-hepten-1-ol: (a) Ti(O-i-Pr)4, L-DIPT, t-BuOOH (87%); (b) Me3Al (75%); (c) PhCH(OMe)2, CSA (74%); (d) DIBAL (95%); (e) IBX (83%). See the Supporting Information for details.
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20 was synthesized in three steps from but-3-enoyloxazolidinone (for which see: Harmat, N. J. S.; Mangani, S.; Perrotta, E.; Giannotti, D.; Nannicini, R.; Altamura, M. Tetrahedron Lett. 2000, 41, 1261. ): (a) LHMDS, benzyl bromoacetate (68%); (b) BnOLi (80%); (c) NaIO4, cat. RuCl3-H2O (91%). See the Supporting Information for details.
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20 was synthesized in three steps from but-3-enoyloxazolidinone (for which see: Harmat, N. J. S.; Mangani, S.; Perrotta, E.; Giannotti, D.; Nannicini, R.; Altamura, M. Tetrahedron Lett. 2000, 41, 1261. ): (a) LHMDS, benzyl bromoacetate (68%); (b) BnOLi (80%); (c) NaIO4, cat. RuCl3-H2O (91%). See the Supporting Information for details.
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48
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Our synthetic fumonisin B1 showed ~50% inhibition of 13C-palmitate incorporation into the sphingoid base backbone of ceramide in RAW264.7 cells when added at 0.1 μM, which is near the Ki for ceramide synthase: Merrill, A. H, Georgia Institute of Technology, Riley, R. T, USDA, Private communication
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Our synthetic fumonisin B1 showed ~50% inhibition of 13C-palmitate incorporation into the sphingoid base backbone of ceramide in RAW264.7 cells when added at 0.1 μM, which is near the Ki for ceramide synthase: Merrill, A. H. (Georgia Institute of Technology); Riley, R. T. (USDA). Private communication.
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49
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For studies of aminodiol compounds similar to the C2-C5 region of fumonisin B1, see: (a) Menaldino, D. S.; Bushnev, A.; Sun, A.; Liotta, D. C.; Symolon, H.; Desai, K.; Dillehay, D. L.; Peng, Q.; Wang, E.; Allegood, J.; Trotman-Pruett, S.; Sullards, M. C.; Merrill, A. H., Jr. Pharmacol. Res. 2003, 47, 373.
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For studies of aminodiol compounds similar to the C2-C5 region of fumonisin B1, see: (a) Menaldino, D. S.; Bushnev, A.; Sun, A.; Liotta, D. C.; Symolon, H.; Desai, K.; Dillehay, D. L.; Peng, Q.; Wang, E.; Allegood, J.; Trotman-Pruett, S.; Sullards, M. C.; Merrill, A. H., Jr. Pharmacol. Res. 2003, 47, 373.
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Errata1
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