Expeditious tandem-metathesis route to the AB-ring fragment of ciguatoxin

Tetrahedron Letters

Volumn 40, Issue 29, 1999, Pages 5405-5408

  Oguri, Hiroki ^a   Sasaki, Shin ya ^a   Oishi, Tohru ^a   Hirama, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Ciguatoxin; Cross metathesis; Diastereoselective ring closing metathesis; Umpolung of allyl palladium

Indexed keywords

CIGUATOXIN; GLUCONATE CALCIUM; TRI O BENZYLGLUCAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033575462     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01017-5     Document Type: Article

References (40)

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4. For recent synthetic studies of cyclic ether systems applying the ring-closing metathesis by other groups, see: a) Nicolaou, K. C.; Postema M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. b) Nicolaou, K. C.; Postema, M. H. D.; Yue, E. W.; Nadin, A. J. Am. Chem. Soc. 1996, 118, 10335. c) Clark J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123. d) Clark J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127. e) Delgado M.; Martín, J. D. Tetrahedron Lett. 1997, 38, 6299. f) Crimmins M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548. g) Clark J. S.; Trevitt, G. P.; Boyall, D.; Stammen, B. Chem. Commun. 1998, 2629. h) Sasaki, M.; Noguchi, T.; Tachibana, K. Tetrahedron Lett. 1999, 40, 1337.
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6. For recent synthetic studies of cyclic ether systems applying the ring-closing metathesis by other groups, see: a) Nicolaou, K. C.; Postema M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. b) Nicolaou, K. C.; Postema, M. H. D.; Yue, E. W.; Nadin, A. J. Am. Chem. Soc. 1996, 118, 10335. c) Clark J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123. d) Clark J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127. e) Delgado M.; Martín, J. D. Tetrahedron Lett. 1997, 38, 6299. f) Crimmins M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548. g) Clark J. S.; Trevitt, G. P.; Boyall, D.; Stammen, B. Chem. Commun. 1998, 2629. h) Sasaki, M.; Noguchi, T.; Tachibana, K. Tetrahedron Lett. 1999, 40, 1337.
7. For recent synthetic studies of cyclic ether systems applying the ring-closing metathesis by other groups, see: a) Nicolaou, K. C.; Postema M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. b) Nicolaou, K. C.; Postema, M. H. D.; Yue, E. W.; Nadin, A. J. Am. Chem. Soc. 1996, 118, 10335. c) Clark J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123. d) Clark J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127. e) Delgado M.; Martín, J. D. Tetrahedron Lett. 1997, 38, 6299. f) Crimmins M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548. g) Clark J. S.; Trevitt, G. P.; Boyall, D.; Stammen, B. Chem. Commun. 1998, 2629. h) Sasaki, M.; Noguchi, T.; Tachibana, K. Tetrahedron Lett. 1999, 40, 1337.
8. For recent synthetic studies of cyclic ether systems applying the ring-closing metathesis by other groups, see: a) Nicolaou, K. C.; Postema M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. b) Nicolaou, K. C.; Postema, M. H. D.; Yue, E. W.; Nadin, A. J. Am. Chem. Soc. 1996, 118, 10335. c) Clark J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123. d) Clark J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127. e) Delgado M.; Martín, J. D. Tetrahedron Lett. 1997, 38, 6299. f) Crimmins M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548. g) Clark J. S.; Trevitt, G. P.; Boyall, D.; Stammen, B. Chem. Commun. 1998, 2629. h) Sasaki, M.; Noguchi, T.; Tachibana, K. Tetrahedron Lett. 1999, 40, 1337.
9. For recent synthetic studies of cyclic ether systems applying the ring-closing metathesis by other groups, see: a) Nicolaou, K. C.; Postema M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. b) Nicolaou, K. C.; Postema, M. H. D.; Yue, E. W.; Nadin, A. J. Am. Chem. Soc. 1996, 118, 10335. c) Clark J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123. d) Clark J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127. e) Delgado M.; Martín, J. D. Tetrahedron Lett. 1997, 38, 6299. f) Crimmins M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548. g) Clark J. S.; Trevitt, G. P.; Boyall, D.; Stammen, B. Chem. Commun. 1998, 2629. h) Sasaki, M.; Noguchi, T.; Tachibana, K. Tetrahedron Lett. 1999, 40, 1337.
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14. For our convergent synthesis of the trans-fused cyclic ether systems based on a ring-closing olefin metathesis, see: a) Oishi, T.; Nagumo, Y.; Hirama, M. SYNLETT 1997, 980. b) Oishi, T.; Nagumo, Y.; Hirama, M. Chem. Commun. 1998, 1041.
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24. For domino process combining different types of metathesis reaction see: a) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634. b) Harrity, J. P. A.; Visser, M. S.; Gleason, J. D.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 1488. c) Stragies, R.; Blechert, S. SYNLETT 1998, 169.
25. For domino process combining different types of metathesis reaction see: a) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634. b) Harrity, J. P. A.; Visser, M. S.; Gleason, J. D.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 1488. c) Stragies, R.; Blechert, S. SYNLETT 1998, 169.
26. For other synthetic studies of the AB(C)-ring fragment, see: a) Oka, T.; Fujiwara, K.; Murai, A. Tetrahedron, 1998, 38, 21. b) Hosokawa, S.; Isobe, M. J. Org. Chem. 1999, 64, 37. c) Rungnapha, S.; Isobe, M. Tetrahedron Lett. 1999, 40, 1911.
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28. For other synthetic studies of the AB(C)-ring fragment, see: a) Oka, T.; Fujiwara, K.; Murai, A. Tetrahedron, 1998, 38, 21. b) Hosokawa, S.; Isobe, M. J. Org. Chem. 1999, 64, 37. c) Rungnapha, S.; Isobe, M. Tetrahedron Lett. 1999, 40, 1911.
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33. The aldehyde (8) was synthesized from cis-2-butene-1,4-diol via silylation followed by ozonolysis.
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36. The carbon numbering corresponding to that of CTX1B has been used throughout this paper.
37. The olefin (15) was synthesized as follows. (formula presented)
38. For ring-opening cross-metathesis, see: a) Snapper, M. L.; Tallarico, J. A.; Randell, M. L. J. Am. Chem. Soc. 1997, 119, 1478. b) Schneider, M. F.; Licas, N.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. 1997, 36, 257. c) Cuny, G. D.; Cao, J. C.; Hauske, J. R. Tetrahedron Lett. 1997, 38, 5237.
39. For ring-opening cross-metathesis, see: a) Snapper, M. L.; Tallarico, J. A.; Randell, M. L. J. Am. Chem. Soc. 1997, 119, 1478. b) Schneider, M. F.; Licas, N.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. 1997, 36, 257. c) Cuny, G. D.; Cao, J. C.; Hauske, J. R. Tetrahedron Lett. 1997, 38, 5237.
40. For ring-opening cross-metathesis, see: a) Snapper, M. L.; Tallarico, J. A.; Randell, M. L. J. Am. Chem. Soc. 1997, 119, 1478. b) Schneider, M. F.; Licas, N.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. 1997, 36, 257. c) Cuny, G. D.; Cao, J. C.; Hauske, J. R. Tetrahedron Lett. 1997, 38, 5237.