A highly efficient synthesis of the hemibrevetoxin B ring system

Organic Letters

Volumn 2, Issue 2, 2000, Pages 231-234

  Rainier, Jon D ^a   Allwein, Shawn P ^a   Cox, Jason M ^a  

^a University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FUSED HETEROCYCLIC RINGS; HEMIBREVETOXIN B; MARINE TOXIN;

ARTICLE; CHEMISTRY; SYNTHESIS; TECHNIQUE;

HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MARINE TOXINS; METHODS;

EID: 0034719251     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991371r     Document Type: Article

References (29)

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2. (a) For the isolation of brevetoxin B, see: Lin, Y. Y.; Risk, M.; Ray, M. S.; VanEnsen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773.
3. (b) For the total synthesis of brevetoxin B, see: Nicolaou, K. C.; Rutjes, F. P. J. T.; Theodorakis, E. A.; Tiebes, J.; Sato, M.; Untersteller, E. J. Am. Chem. Soc. 1995, 117, 10252.
4. (c) For the isolation of brevetoxin A, see: Shimizu, Y.; Chou, H. -N.; Bando, H.; Van Duyne, G.; Clardy, J. C. J. Am. Chem. Soc. 1986, 108, 514.
5. (d) For the total synthesis of brevetoxin A, see: Nicolaou, K. C.; Yang, Z.; Shi, G.-Q.; Gunzner, J. L.; Agrios, K. A.; Gärtner, P. Nature 1998, 392, 264.
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16. (b) Rainier, J. D.; Allwein, S. P. Tetrahedron Lett. 1998, 39, 9601.
17. Hemibrevetoxin B syntheses with number of transformations. (a) Nicolaou group: 54 synthetic steps from D-mannose. Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc. 1993, 115, 3558.
18. (b) Yamamoto group: 52 steps from D-mannose. Kadota, I.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6597.
19. (c) Nakata group: 61 steps from geranyl acetate. Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365.
20. (d) Mori group: 36 steps from tri-O-acetyl-D-glucal to a Yamamoto intermediate, 43 steps overall. Mori, Y.; Yaegassi, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200.
21. Danishefsky, S.; Kitahara, T.; Schuda, P. F. Org. Synth. 1983, 61, 147.
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23. Others have also utilized hetero-Diels-Alder chemistry to the hemibrevetoxin A-ring. See: (a) Gleason, M. M.; McDonald, F. E. J. Org. Chem. 1997, 62, 6432.
24. (b) Saleh, T.; Rousseau, G. Synlett 1999, 617.
25. It is possible to generate 11 in enantiomerically enriched form using Keck's binol protocol. See ref 11 and Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998.
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27. We have determined that the cyclized product in this reaction comes from an olefin metathesis, carbonyl olefination process. Rainier, J. D.; Cox, J. M. Unpublished results.
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29. We currently believe that the effect of a noncoordinating solvent (hexanes) is to favor the intramolecular delivery of the methyl nucleophile from an aluminum-ate complex.