Total synthesis of brevetoxin A

Nature

Volumn 392, Issue 6673, 1998, Pages 264-269

  Nicolaou, K C ^a   Yang, Zhen ^b   Shi, Guo Qiang ^b   Gunzner, Janet L ^b   Agrlos, Konstantinos A ^b   Gärtner, Peter ^b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

BREVETOXIN; MARINE TOXIN; NEUROTOXIN; SODIUM CHANNEL;

ARTICLE; CHEMICAL STRUCTURE; MARINE ENVIRONMENT; NEUROTOXICITY; NONHUMAN; PRIORITY JOURNAL; SYNTHESIS; TOXIN ANALYSIS;

ANIMALS; DINOFLAGELLIDA; MARINE TOXINS; NEUROTOXINS; OXOCINS;

ALGAE; GYMNODINIUM; KARENIA BREVIS;

EID: 0032546365     PISSN: 00280836     EISSN: None     Source Type: Journal    
DOI: 10.1038/32623     Document Type: Article

References (45)

1. Shimizu, Y., Chou, H.-N. & Bando, H. Structure of brevetoxin A (GB-1 toxin), the most potent toxin in the Florida red tide organism Gymnodinium breve (Ptychodiscua brevis). J. Am. Chem. Soc. 108, 514-515 (1986).
2. Shimizu, Y., Bando, H., Chou, H.-N., Van Duyne, G. & Clardy, J. C. Absolute configuration of brevetoxins. J. Chem. Soc., Chem. Commun. 1656-1658 (1986).
3. Pawlak, J. et al. Structure of brevetoxin A as constructed from NMR and MS data. J. Am. Chem. Soc. 109, 1144-1150 (1987).
4. Rein, K. S., Baden, D. G. & Gawley, R. E. Conformationl analysis of the sodium channel modulator, brevetoxin A, comparison with brevetoxin B conformations, and a hypothesis about the common pharmacophore of the "site 5" toxins. J. Org. Chem. 59, 2101-2106 (1994).
5. Rein, K. S., Lynn, B., Baden, D. G. & Gawley, R. E. Brevetoxin B: chemical modifications, synaptosome binding, toxicity, and an unexpected conformational effect. J. Org. Chem. 59, 2107-21013 (1994).
6. Yasumoto, T. & Murata, M. Marine toxins. Chem. Rev. 93, 1897-1909 (1993).
7. Gawley, R. E. et al. The relationship of brevetoxin "length" and A-ring functionality to binding and activity in neuronal sodium channels. Chem. Biol. 2, 533-541 (1995).
8. Chou, H.-N. & Shimizu, Y. Biosynthesis of brevetoxins. Evidence for the mixed origin of the backbone carbon chain and the possible involvement of dicarboxylic acids. J. Am, Chem. Soc. 109, 2184-2185 (1987).
9. Lee, M. S., Qin, G.-W., Nakanishi, K. & Zagorski, M. G. Biosynthesis studies on brevetoxins, potent neurotoxins produced by the dinoflagellate Gymnodinium breve. J. Am, Chem. Soc. 111, 6234-6241 (1969).
10. Nicolaou, K. C., Prasad, C. V. C., Hwang, C.-K., Duggan, M. E. & Veale, C. A. Cyclizations of hydroxydithioketals. New synthetic technology for the construction of oxocenes and related medium ring systems. J. Am. Chem. Soc. 111, 5321-5330 (1989).
11. Nicolaou, K. C., Shi, G.-Q., Gunzner, I. L., Gärtner, P. & Yang, Z. Palladium-catalyzed functionalization of lactones via their cyclic ketene acetal phosphates. Efficient new synthetic technology for the construction of medium and large cyclic ethers. J. Am. Chem. Soc. 119, 5467-5468 (1997).
12. Nicolaou, K. C., Prasad, C. V. C., Somers, P. K. & Hwang, C.-K. Activation of 6-endo over 5-exo hydroxy epoxide openings. Stereo- and ringselective synthesis of tetrahydrofuran and tetrahydropyran systems. J. Am. Chem. Soc. 111, 5330-5334 (1989).
13. Freeman, J. P. in Organic Syntheses (Collective Vol. VII) 139-141 (Wiley, New York, 1990).
14. Xie, M., Beges, D. A. & Robins, M. J. Efficient "dehomologation" of di-O-isopropylidenehexofuranose derivatives to give O-isopropylidenepentofuranose by sequential treatment with periodic acid in ethyl acetate and sodium borohydride. J. Org. Chem. 61, 5178-5179 (1996).
15. Mukaiyama, T., Banno, K. & Narasaka, K. New cross-aldol reactions. Reactions of silyl enol ethers with carbonyl compounds activated by titanium tetrachloride. J. Am. Chem. Soc. 96, 7503-7509 (1974).
16. Rodeheaver, G. T. & Hunt, D. F. Conversion of olefins into ketones with mercuric acetate and palladium chloride. Chem. Commun. 818-819 (1971).
17. Tamura, Y., Ochiai, H., Nakamura, T. & Yoshida, Z. Arylation and vinylation of 2-carboethoxyethyl-zinc iodide and 3-carboethoxypropylzinc iodide catalyzed by palladium. Tetrahedr. Lett. 27, 955-958 (1986).
18. Inanaga, I., Hirata, K., Saeki, H., Katsuki, T. & Yamaguchi, M. A rapid esterification by mixed anhydride and its application to large-ring lactonization. Bull. Chem. Soc. Jpn 52, 1989-1993 (1979).
19. Arhart, R. J. & Martin, J. C. Sulfuranes, V. The chemistry of sulfur (IV) compounds. Dialkoxydiarylsulfuranes. J. Am. Chem. Soc. 94, 4997-5003 (1972).
20. Hoveyda, A. H., Evans, D. A. & Fu, G. C. Substrate-directable chemical reactions. Chem. Rev. 93, 1307-1370 (1993).
21. Nicolaou, K. C., McGarry, D. G. & Sommers, P. K. New synthetic strategies for the construction of medium-size cyclic ethers. Stereocontrolled synthesis of the BCD ring framework of brevetoxin A. J. Am. Chem. Soc. 112, 3696-3697 (1990).
22. 2CuLi which allow selective group transfer. J. Am. Chem. Soc. 94, 7210-7211 (1972).
23. -, TPAP: a catalytic oxidant for organic synthesis, Synthesis 639-666 (1994).
24. Nicolaou, K. C. et al. New synthetic technology for the construction of 9-membered ring cyclic ethers. Construction of the EFGH ring skeleton of brevetoxin A. J. Am, Chem. Soc. 119, 8105-8106 (1997).
25. 6. J. Am. Chem. Soc. 119, 8105-8106 (1997).
26. Feixas, J., Capdevila, A. & Guerrero, A. Utilization of neutral alumina as a mild reagent for the selective cleavage of primary and secondary silyl ethers. Tetrahedron 50, 8539-8550 (1994).
27. Nicolaou, K. C. et al. Novel strategies for the construction of complex polycyclic ether frameworks. Stereocontrolled synthesis of the FGHIJ ring system of brevetoxin A. Angew. Chem. Int. Edn. Engl. 30, 299-303 (1991).
28. Parikh, J. R. & Doering, W. von E. Sulfur trioxide in the oxidation of alcohols by dimethyl sulfoxide. J. Am. Chem. Soc. 89, 5505-5507 (1967).
29. Clayden, J. & Warren, S. Stereocontrol in organic synthesis using the diphenylphosphoryl group. Angew. Chem. Int. Edn. Engl. 35, 241-270 (1996).
30. 13C NMR peaks of brevetoxin A: application of two-dimensional Hartmann-Hahn spectroscopy. J. Org. Chem. 53, 4156-4157 (1988).
31. 13. New J. Chem. 11, 753-756 (1987).
32. Klindgren, B. O. & Nilsson, T. Preparation of carboxylic acids from aldehydes (including hydroxylated benzaldehydes) by oxidation with chloritc. Acta Chem. Scand. 27, 888-890 (1973).
33. Dess, D. B. & Martin, J. C. Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones. J. Org. Chem. 48, 4155-4156 (1983).
34. Schreiber, J., Maag, H., Hashimoto, N. & Eschenmoser, A. Dimethyl(methylene)ammonium iodide. Angew. Chem. Int. Edn. Engl. 10, 330-331 (1971).
35. Nicolaou, K. C. et al. Total synthesis of brevetoxin B. 1. First generation strategies and new approaches to oxepane systems. J. Am. Chem. Soc. 117, 10227-10238 (1995).
36. Nicolaou, K. C. et al. Total synthesis of brevetoxin B. 2. Second generation strategies and construction of the dioxepane region [DEFG]. J. Am. Chem. Soc. 117, 10239-10231 (1995).
37. Nicolaou, K. C. et al. Total synthesis of brevetoxin B. 3. Final strategy and completion. J. Am. Chem. Soc. 117, 10252-10263 (1995).
38. Nicolaou, K. C. The total synthesis of brevetoxin B: a twelve year odyssey in organic synthesis. Angew. Chem. Int. Edn. Engl. 33, 589-607 (1996).
39. Homaka, Y. Recent methods for detection of seafood toxins: recent immunological method for ciguatoxin and related polyethers. Food Addit. Contam. 10, 71-82 (1993).
40. Anderson, D. M. Turning back the harmful red tide. Nature 388, 513-514 (1997).
41. Barker, R. And the Waters Turned to Blood (Simon & Schuster, New York, 1997).
42. Anderson, D. M. Red tides. Sci. Am. 271, 62-68 (1994).
43. Hall, S. & Strichartz, G. (eds) (American Chemical Society, Washington DC, 1990).
44. Okaichi, T., Anderson, D. M. & Nemoto, T. (eds) Red Tides. Biology, Environmental Science, and Toxicology (Elsevier, New York, 1989).
45. Anderson, D. M. & White, A. W. Marine biotoxins, at the top of the food chain. Oceanus 35, 55-61 (1992).