Studies towards total synthesis of antillatoxin: Synthesis of C1-C11 fragment

Tetrahedron Letters

Volumn 39, Issue 11, 1998, Pages 1457-1460

  Loh, Teck Peng ^a   Cao, Guo Qiang ^a   Pei, Jian ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM CHLORIDE; LANTHANIDE; ORGANIC COMPOUND; TOXIN;

ARTICLE; CATALYSIS; TOXIN SYNTHESIS;

EID: 0032510431     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10827-9     Document Type: Article

References (19)

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2. 2. For another synthetic study towards the total synthesis of antillatoxin, refer to: Wardrop D. and White J. D. 213th ACS National Meeting, ACS division of Organic Chemistry (San Francisco), No. 399, April 13-17, 1997.
3. 3. For the pioneering work on the indium-mediated allylation reaction of carbonyl compounds in water, refer to: (a) Li, C. J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017.
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11. 7. Lanthanide triflate has been shown to increase the rate and selectivity of indium-mediated allylation reaction of carbonyl compounds (a) Wang, R-B.; Lim, C.-M.; Tan, C.-H.; Lim, B.-K.; Sim, K-Y.; Loh, T.-P. Tetrahedron: Asymmetry, 1995, 6, 1825-1828.
12. (b) Ho, Diana, S.-C.; Sim, K.-Y. and Loh, T.-P. Synlett, 1996, 263-264.
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14. 8. Loh, T.-P.; Cao, G.-Q.; Jian, P. submitted for publication.
15. 9. Maguire, R. J.; Mulzer, J. and Bats, J. W. J. Org. Chem. 1996, 61, 6936-6940.
16. 10. (a) Kiji, J.; Okano, T.; Konishi, H. and Nishiumi, W. Chemistry Letters, 1989, 1873-1876.
17. (b) Okano, T.; Okabe, N. and Kiji, T. Bull. Chem. Soc. Jpn. 1992, 65, 2589-2593.
18. 11. Syn selectivity using (Z)-2-(bromomethyl)-2-butenoate as the halide source has been reported: Isaac, M. B.; Paquette, L. A. J. Org. Chem. 1997, 62, 5333-5338.
19. 12. This research was assisted financially by the National University of Singapore (RP 940633, RP950609, RP970615 and RP970616).