Total synthesis of a chlorosulpholipid cytotoxin associated with seafood poisoning

Nature

Volumn 457, Issue 7229, 2009, Pages 573-576

  Nilewski, Christian ^a   Geisser, Roger W ^a   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROSULPHOLIPID; CYTOTOXIN; HYDROCARBON; MARINE TOXIN; NATURAL PRODUCT; POLYCHLORINATED HYDROCARBON; UNCLASSIFIED DRUG;

BIOACTIVITY; FOOD POISONING; HEALTH RISK; LIPID; PUBLIC HEALTH; SEAFOOD; SUBSTRATE; TOXIN;

ARTICLE; BIOLOGICAL ACTIVITY; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; DRUG SYNTHESIS; FOOD POISONING; HEALTH HAZARD; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MELTING POINT; MEMBRANE; MOLECULAR MODEL; NONHUMAN; ORGANIC CHEMISTRY; ORGANISM; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SEA FOOD; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; TOXIN SYNTHESIS;

ALCOHOLS; ALGAE; CHLORINE; CIGUATERA POISONING; CYTOTOXINS; EPOXY COMPOUNDS; HUMANS; HYDROCARBONS, CHLORINATED; LIPIDS; MOLECULAR STRUCTURE;

EID: 59049083939     PISSN: 00280836     EISSN: 14764687     Source Type: Journal    
DOI: 10.1038/nature07734     Document Type: Article

References (27)

1. Ahmed, F. E. Naturally occurring seafood toxins. J. Toxicol. Toxin Rev. 10, 263-287 (1991).
2. Ciminiello, P. & Fattorusso, E. Shellfish toxins - Chemical studies on Northern Adriatic mussels. Eur. J. Org. Chem. 2004, 2533-2551 (2004).
3. Yasumoto, T. & Murata, M. Marine toxins. Chem. Rev. 93, 1897-1909 (1993).
4. Elovson, J. & Vagelos, P. R. A new class of lipids: Chlorosulfolipids. Proc. Natl Acad. Sci. USA 62, 957-963 (1969).
5. Elovson, J. & Vagelos, P. R. Structure of the major species of chlorosulfolipid from Ochromonas danica. 2,2,11,13,15,16-hexachloro-N- docosane 1,14-disulfate. Biochemistry 9, 3110-3126 (1970).
6. Haines, T. H. Halogen- and sulfur-containing lipids of Ochromonas. Annu. Rev. Microbiol. 27, 403-411 (1973).
7. Mercer, E. I. & Davies, C. L. Chlorosulpholipids of Tribonema aequale. Phytochemistry 13, 1607-1610 (1974).
8. Mercer, E. I. & Davies, C. L. Chlorosulpholipids in algae. Phytochemistry 14, 1545-1548 (1975).
9. Chen, J. L., Proteau, P. J., Roberts, M. A. & Gerwick, W. H. Structure of malhamensilipin A, an inhibitor of protein tyrosine kinase, from the cultured chrysophyte Poterioochromonas malhamensis. J. Nat. Prod. 57, 524-527 (1994).
10. Ciminiello, P. et al. Structural elucidation of a new cytotoxin isolated from mussels of the Adriatic Sea. J. Org. Chem. 66, 578-582 (2001).
11. Ciminiello, P. et al. Structure and stereochemistry of a new cytotoxic polychlorinated sulfolipid from Adriatic shellfish. J. Am. Chem. Soc. 124, 13114-13120 (2002).
12. Ciminiello, P. et al. A new cytotoxic polychlorinated sulfolipid from contaminated Adriatic mussels. Tetrahedron 60, 7093-7098 (2004).
13. Shibuya, G. M., Kanady, J. S. & Vanderwal, C. D. Stereoselective dichlorination of allylic alcohol derivatives to access key stereochemical arrays of the chlorosulfolipids. J. Am. Chem. Soc. 130, 12514-12518 (2008).
14. Yoshimitsu, T., Fukumoto, N. & Tanaka, T. Enantiocontrolled synthesis of polychlorinated hydrocarbon motifs: A nucleophilic multiple chlorination process revisited. J. Org. Chem. 74, 696-702 (2009).
15. Hunter, L., O'Hagan, D. & Slawin, A. M. Z. Enantioselective synthesis of an all-syn four vicinal fluorine motif. J. Am. Chem. Soc. 128, 16422-16423 (2006).
16. Nakata, T. Total synthesis of marine polycyclic ethers. Chem. Rev. 105, 4314-4347 (2005).
17. Kang, S. H., Kang, S. Y., Lee, H.-S. & Buglass, A. J. Total synthesis of natural tert-alkylamino hydroxy carboxylic acids. Chem. Rev. 105, 4537-4558 (2005).
18. Matsumori, N., Kaneno, D., Murata, M., Nakamura, H. & Tachibana, K. Stereochemical determination of acyclic structures based on carbon-proton spin-coupling constants. A method of configuration analysis for natural products. J. Org. Chem. 64, 866-876 (1999).
19. Schlama, T., Gabriel, K., Gouverneur, V. & Mioskowski, C. Tetraethylammonium trichloride: A versatile reagent for chlorinations and oxidations. Angew. Chem. Int. Edn Engl. 36, 2342-2344 (1997).
20. Cha, J. K., Christ, W. J. & Kishi, Y. On stereochemistry of osmium tetraoxide oxidation of allylic alcohol systems - Empirical rule. Tetrahedron 40, 2247-2255 (1984).
21. 2 system. J. Am. Chem. Soc. 108, 7408-7410 (1986).
22. Kozminski, W. & Nanz, D. HECADE: HMQC- and HSQC-based 2D NMR experiments for accurate and sensitive determination of heteronuclear coupling constants from E.COSY-type cross peaks. J. Magn. Reson. 124, 383-392 (1997).
23. Petersen, P. E. et al. Solvents of low nucleophilicity. IX. Inductive and participation effects in carbonium ion reactions in acetic, formic, and trifluoroacetic acid. J. Am. Chem. Soc. 89, 5902-5911 (1967).
24. Petersen, P. E., Indelicato, J. M. & Bonazza, B. R. Halogen participation in the protonation of 5-halo-epoxides with trifluoroacetic acid. Tetrahedr. Lett. 12, 13-16 (1971).
25. MacCoss, R. N., Balskus, E. P. & Ley, S. V. A sequential tetra-n-propylammonium perruthenate (TPAP)-Wittig oxidation olefination protocol. Tetrahedr. Lett. 44, 7779-7781 (2003).
26. Paddon-Row, M. N., Rondan, N. G. & Houk, K. N. Staggered models for asymmetric induction: Attack trajectories and conformations of allylic bonds from ab initio transition structures of addition reactions. J. Am. Chem. Soc. 104, 7162-7166 (1982).
27. Pangborn, A. B., Giardello, M. A., Grubbs, R. H., Rosen, R. K. & Timmers, F. J. Safe and convenient procedure for solvent purification. Organometallics 15, 1518-1520 (1996).