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Volumn 131, Issue 17, 2009, Pages 6066-6067

Total synthesis of the sphingolipid biosynthesis inhibitor fumonisin B 1

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHESIS INHIBITORS; CONVERGENT SYNTHESIS; CROSS-COUPLINGS; DEPROTECTION; EFFICIENT SYNTHESIS; FUMONISIN; FUNCTIONALIZED; HOMOALLYLIC ALCOHOL; OXONIA-COPE REARRANGEMENT; SPHINGOLIPIDS; TOTAL SYNTHESIS; TRICARBALLYLIC ACID;

EID: 70149088996     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9009265     Document Type: Article
Times cited : (43)

References (51)
  • 30
    • 33646074058 scopus 로고    scopus 로고
    • For our previous work in this area, see
    • For our previous work in this area, see: Chen, Y.-H.; McDonald, F. E. J. Am. Chem. Soc. 2006, 128, 4568.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 4568
    • Chen, Y.-H.1    McDonald, F.E.2
  • 33
    • 70149101605 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 47
    • 0034685247 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 48
    • 84869622638 scopus 로고    scopus 로고
    • 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
    • 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.
  • 49
    • 12244267059 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 51
    • 34547185997 scopus 로고    scopus 로고
    • Errata: Org. Lett. 2007, 9, 2959.
    • (2007) Org. Lett , vol.9 , pp. 2959
    • Errata1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.