Asymmetric Synthesis of Syringolide 1, a Novel Nonproteinaceous Elicitor

Synlett

Volumn 1996, Issue 4, 1996, Pages 335-336

  Ishihara, Jun ^a   Sugimoto, Tetsuya ^a   Murai, Akio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001468010     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5430     Document Type: Article

References (11)

1. Murai, A. Pesticide Science and Biotechnology ed. by R. Greenhalgh and T. R. Roberts, Blackwell, London, p. 81 (1987).
2. Smith, M. J.; Mazzola, E. P.; Sims, J. J.; Midland, S. L.; Keen, N. T; Burton, V.; Stayton, M. M. Tetrahedron Lett. 1993, 34, 223.; Midland, S. L.;. Keen, N. T; Sims, J. J.; Midland, M. M.; Stayton, M. M. Burton, V.; Smith, M. J.; Mazzola, E. P.; Gragam, K. J.; Clardy, J. J. Org. Chem. 1993, 58, 2940.
3. Smith, M. J.; Mazzola, E. P.; Sims, J. J.; Midland, S. L.; Keen, N. T; Burton, V.; Stayton, M. M. Tetrahedron Lett. 1993, 34, 223.; Midland, S. L.;. Keen, N. T; Sims, J. J.; Midland, M. M.; Stayton, M. M. Burton, V.; Smith, M. J.; Mazzola, E. P.; Gragam, K. J.; Clardy, J. J. Org. Chem. 1993, 58, 2940.
4. Very recently total syntheses of syringolides 1 and 2 were reported: Wood, J. L.; Jeong, S.; Salcedo, A.; Jenkins, J. J. Org. Chem. 1995, 60, 286., Kuwahara, S.; Moriguchi, M.; Miyagawa, K.; Konno, M.; Kodama, O., Tetrahedron Lett. 1995, 36, 3201.; idem, Tetrahedron 1995, 51, 8809.
5. Very recently total syntheses of syringolides 1 and 2 were reported: Wood, J. L.; Jeong, S.; Salcedo, A.; Jenkins, J. J. Org. Chem. 1995, 60, 286., Kuwahara, S.; Moriguchi, M.; Miyagawa, K.; Konno, M.; Kodama, O., Tetrahedron Lett. 1995, 36, 3201.; idem, Tetrahedron 1995, 51, 8809.
6. Very recently total syntheses of syringolides 1 and 2 were reported: Wood, J. L.; Jeong, S.; Salcedo, A.; Jenkins, J. J. Org. Chem. 1995, 60, 286., Kuwahara, S.; Moriguchi, M.; Miyagawa, K.; Konno, M.; Kodama, O., Tetrahedron Lett. 1995, 36, 3201.; idem, Tetrahedron 1995, 51, 8809.
7. Home, D. A.; Fugmann, B.; Yakushijin, K.; Büchi, G. J. Org. Chem. 1993, 58, 62.
8. 2). The preparation of the stannane, see: Wender, P. A.; Sieburth, S. M.; Petraotis, J. J.; Singh, S. K. Tetrahedron 1981, 37, 3967.
9. For review see; Kolb, H., C.; VanNieuwnhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
10. The absolute stereochemistries at C-1', 2 and 3 were not determined. The enantiomeric ratios were determined by the respective bis-MTPA esters corresponding to four isomers of 8.
11. 3)}, since we used compound 8aa, which was estimated to be 87%ee.