Synthesis of medium-sized cyclic allylic ethers by ring-closing metathesis and subsequent elaboration to sub-units found in the brevetoxins and ciguatoxins

Tetrahedron Letters

Volumn 39, Issue 45, 1998, Pages 8321-8324

  Clark, J Stephen ^a   Hamelin, Olivier ^a   Hufton, Richard ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Brevetoxins; Ciguatoxins; Cyclic ethers; Ring closing metathesis

Indexed keywords

ALLYL COMPOUND; BREVETOXIN; CIGUATOXIN; EPOXIDE; ETHER DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032487811     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01825-5     Document Type: Article

References (25)

1. 1. For a review of marine toxins, see: Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897.
2. 2. For recent syntheses of brevetoxins A and B, see: Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 589; Nicolaou, K. C.; Yang, Z.; Shi, G.-Q.; Gunzner, J. L.; Agrios, K. A.; Gärtner, P. Nature 1998, 392, 264.
3. 2. For recent syntheses of brevetoxins A and B, see: Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 589; Nicolaou, K. C.; Yang, Z.; Shi, G.-Q.; Gunzner, J. L.; Agrios, K. A.; Gärtner, P. Nature 1998, 392, 264.
4. 3. Satake, M.; Murata, M.; Yasumoto, T. Tetrahedron Lett. 1993, 34, 1975.
5. 4. For reviews concerning the use of ring-closing metathesis in synthesis, see: Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446; Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833; Armstrong, S. K. J. Chem. Soc., Perkin Trans. I 1998, 371; Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
6. 4. For reviews concerning the use of ring-closing metathesis in synthesis, see: Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446; Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833; Armstrong, S. K. J. Chem. Soc., Perkin Trans. I 1998, 371; Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
7. 4. For reviews concerning the use of ring-closing metathesis in synthesis, see: Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446; Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833; Armstrong, S. K. J. Chem. Soc., Perkin Trans. I 1998, 371; Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
8. 4. For reviews concerning the use of ring-closing metathesis in synthesis, see: Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446; Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833; Armstrong, S. K. J. Chem. Soc., Perkin Trans. I 1998, 371; Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
9. 4. For reviews concerning the use of ring-closing metathesis in synthesis, see: Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446; Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833; Armstrong, S. K. J. Chem. Soc., Perkin Trans. I 1998, 371; Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
10. 5. Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127.
11. 6. For reports concerning the synthesis of brevetoxin and ciguatoxin systems by ring-closing metathesis, subsequent to our own, see: Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548; Delgado, M.; Martín, J. D. Tetrahedron Lett. 1997, 38, 6299; Oishi, T.; Nagumo, Y.; Hirama, M. Chem. Commun. 1998, 1041.
12. 6. For reports concerning the synthesis of brevetoxin and ciguatoxin systems by ring-closing metathesis, subsequent to our own, see: Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548; Delgado, M.; Martín, J. D. Tetrahedron Lett. 1997, 38, 6299; Oishi, T.; Nagumo, Y.; Hirama, M. Chem. Commun. 1998, 1041.
13. 6. For reports concerning the synthesis of brevetoxin and ciguatoxin systems by ring-closing metathesis, subsequent to our own, see: Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548; Delgado, M.; Martín, J. D. Tetrahedron Lett. 1997, 38, 6299; Oishi, T.; Nagumo, Y.; Hirama, M. Chem. Commun. 1998, 1041.
14. 7. Schwab, P.; France, M. B.; Ziller J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039.
15. 8. For a review of methods available for the preparation of (R)-2,3-O-isopropylideneglyceraldehyde and the use of this compound in synthesis, see: Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron 1986, 42, 447.
16. 9. Mulzer, J.; Angermann, A. Tetrahedron Lett. 1983, 24, 2843.
17. 10. Schrock R. R.; Murdzek, J. S; Bazan, G. C.; Robbins, J.; DiMare M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875.
18. 11. For the epoxidation of a related cylic allylic ether using m-CPBA, see: Atsuta, H.; Fujiwara, K.; Murai, A. Synlett 1997, 307.
19. 12. Treatment of the cyclic allylic ether 6a with dimethyldioxirane in dichloromethane at 0 °C for 26 h afforded the epoxides 7a and 8a in 42% and 27% yield respectively along with unreacted allylic ether (20%).
20. 13. Boehm, M. F.; Prestwich, G. D. J. Org. Chem. 1986, 51, 5447; Askin, D.; Angst, C.; Danishefsky, S. J. Org. Chem. 1987, 52, 622.
21. 13. Boehm, M. F.; Prestwich, G. D. J. Org. Chem. 1986, 51, 5447; Askin, D.; Angst, C.; Danishefsky, S. J. Org. Chem. 1987, 52, 622.
22. 14. For an example of ring-opening of a related epoxide using lithium triethylborohydride, see: Armistead, D. M.; Danishefsky, S. J. Tetrahedron Lett. 1987, 28, 4959.
23. 15. Crandall, J. K.; Apparu, M. Org. React. 1983, 29, 345.
24. 16. Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc. 1973, 95, 2697.
25. 17. Faulkner, D. J. Nat. Prod. Rep. 1998, 75, 113 and references therein.