Enantioselective total synthesis of fumonisin B2

Journal of Organic Chemistry

Volumn 62, Issue 17, 1997, Pages 5666-5667

  Shi, Yan ^a   Peng, Lee F ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FUMONISIN B2; MYCOTOXIN; NATURAL PRODUCT;

ARTICLE; CHIRALITY; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; STEREOCHEMISTRY; TOXIN ANALYSIS; TOXIN STRUCTURE;

EID: 0030773366     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9711347     Document Type: Article

References (29)

1. (a) For the stereochemistry assignment of the AAL toxins and fumonisins from this and other groups up to the beginning of 1995, see: Boyle, C. D.; Kishi, Y. Tetrahedron Lett. 1995, 36, 5695 and references cited therein.
2. (b) For more recent work on this subject, see: Blackwell, B. A.; Edwards, O. E.; Fruchier, A.; ApSimon, J. W.; Miller, J. D. Fumonisins in Food; Jackson, L., et al., Eds.; Plenum Press: New York, 1996; pp 75-91 and references cited therein.
3. For the stereochemistry assignment of maitotoxin, see: (a) Zheng, W.; Demattei, J. A.; Wu, J.-P.; Duan, J. J.-W.; Cook, L. R.; Oinuma, H.; Kishi, Y. J. Am. Chem. Soc. 1996, 118, 7946. (b) Nonomura, T.; Sasaki, M.; Matsumori, N.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1675 and references cited therein.
4. For the stereochemistry assignment of maitotoxin, see: (a) Zheng, W.; Demattei, J. A.; Wu, J.-P.; Duan, J. J.-W.; Cook, L. R.; Oinuma, H.; Kishi, Y. J. Am. Chem. Soc. 1996, 118, 7946. (b) Nonomura, T.; Sasaki, M.; Matsumori, N.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1675 and references cited therein.
5. Bezuidenhout, S. C.; Gelderblom, W. C. A.; Gorst-Allman, C. P.; Horak, R. M.; Marasas, W. F. O.; Spiteller, G.; Vleggaar, R. J. Chem. Soc., Chem. Commun. 1988, 743.
6. For examples, see: (a) Mycopathologia 1992, 117, pp 1-124 for 18 reviews regarding various aspects of biological activity of fumonisins and AAL toxins, (b) Merrill, A. H., Jr.; Wang, E.; Gilchrist, D. G.; Riley, R. T. Adv. Lipid Res. 1993, 26, 215.
7. For examples, see: (a) Mycopathologia 1992, 117, pp 1-124 for 18 reviews regarding various aspects of biological activity of fumonisins and AAL toxins, (b) Merrill, A. H., Jr.; Wang, E.; Gilchrist, D. G.; Riley, R. T. Adv. Lipid Res. 1993, 26, 215.
8. 1H NMR spectrum of its (-)-menthol ester, and its absolute configuration was established by a chemical correlation with a known compound [Boyle, C. D.; Kishi, Y. Tetrahedron Lett. 1995, 36, 4579].
9. 1H NMR spectrum of its (-)-menthol ester, and its absolute configuration was established by a chemical correlation with a known compound [Boyle, C. D.; Kishi, Y. Tetrahedron Lett. 1995, 36, 4579].
10. 2, cf. the structure 1.
11. 1H NMR spectrum of its Mosher ester.
12. 1H NMR spectrum of its Mosher ester.
13. 1H NMR spectrum of its Mosher ester.
14. Mancuso, A.; Huang, S.-L.; Swern, D. J. Org. Chem. 1978, 43, 2480.
15. Kraus, G. A.; Taschner, M. J. J. Org. Chem. 1980, 45, 1175.
16. For reviews on this subject, see: (a) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321. (b) Bartlett, P. A.; Richardson, D. P.; Myerson, J. Tetrahedron 1984, 40, 2317.
17. For reviews on this subject, see: (a) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321. (b) Bartlett, P. A.; Richardson, D. P.; Myerson, J. Tetrahedron 1984, 40, 2317.
18. Previous work in this laboratory showed that the installation of the C14 and C15 hydroxyl groups via dihydroxylation of a cis-olefin without the use of a chiral ligand resulted in a 1:3 ratio of desired to undesired diols, with the best result being a 1:1 ratio of desired to undesired diols using the Sharpless DHQ-IND ligand. See: (a) the supporting information of Boyle, C. D.; Harmange, J.-C.; Kishi, Y. J. Am. Chem. Soc. 1994, 116, 4995. (b) Boyle, C. D. Ph.D. Thesis, Harvard University, 1995.
19. Previous work in this laboratory showed that the installation of the C14 and C15 hydroxyl groups via dihydroxylation of a cis-olefin without the use of a chiral ligand resulted in a 1:3 ratio of desired to undesired diols, with the best result being a 1:1 ratio of desired to undesired diols using the Sharpless DHQ-IND ligand. See: (a) the supporting information of Boyle, C. D.; Harmange, J.-C.; Kishi, Y. J. Am. Chem. Soc. 1994, 116, 4995. (b) Boyle, C. D. Ph.D. Thesis, Harvard University, 1995.
20. Fehrentz, J-A.; Castro, B. Synthesis 1983, 676.
21. 4 reduction followed by esterification.
22. Brown, H. C.; Bhat, K. S.; Randad, R. S. J. J. Org. Chem. 1989, 54, 1570.
23. When (+)-B-allyldiisopinocampheylborane was employed, the anti-amino alcohol corresponding to 12 was obtained in 94% de.
24. When (-)-B-allyldiisopinocampheylborane was used, the synalcohol corresponding to 13 was obtained in greater than 18:1 ratio.
25. The choice of solvents for hydrogenation/hydrogenolysis is important. For example, conducting the reduction in methanol led to the formation of methyl esters.
26. 2 was purchased from the South African Research Council, Tygerberg, South Africa, and was isolated from the Fusarium moniliforme strain MRC 826.
27. 2 (see the spectra attached in Supporting Information), thereby confirming our previous conclusion.
28. 2 (see the spectra attached in Supporting Information), thereby confirming our previous conclusion.
29. 2 remote diastereomers. In addition, the olefin 12 provides easy access to analogs with different tether lengths or different tethers between the two structural motifs. We will study the biological behaviors of these analogs, in reference to the eicosane derivatives bearing only the left-half or right-half functional groups.