Heteroconjugate addition strategy for the synthesis of the (HIJ)K-ring fragment of ciguatoxin

Synlett

Volumn , Issue 5, 2000, Pages 587-590

  Liu, Tong Zhu ^a   Kirschbaum, Bettina ^a   Isobe, Minoru ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Biscobalthexacarbonyl complex; Ciguatoxin; Heteroconjugate addition; Oxepane cyclization

Indexed keywords

CIGUATOXIN;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; NONHUMAN; STEREOCHEMISTRY; SYNTHESIS; TOXIN ANALYSIS; TOXIN STRUCTURE;

EID: 0034077809     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (18)

1. For recent reviews on ciguatoxin and related marine toxins, see: (a) Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897-1909.
2. (b) Scheuer, P. J. Tetrahedron 1994, 50, 3-18.
3. For recent synthetic studies from other groups, see: (a) Sasaki, M.; Noguchi, T.; Tachibana, K. Tetrahedron Lett. 1999, 40, 1337-1340.
4. (b) Sasaki, M.; Fuwa, H.; Ishikawa, M.; Tachibana, K. Organic Lett. 1999, 1, 1075-1077.
5. (c) Oguri, H.; Sakaki, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1999, 40, 5405-5408.
6. Maeda, K.; Oishi, T.; Oguri, H.; Hirama, M. Chem. Comm. 1999, 1063-1064.
7. (e) Oishi, T.; Nagumo, Y.; Shoji, M.; Brazidec, J.-Y. L.; Uehara, H.; Hirama, M. Chem. Comm. 1999, 2035-2036.
8. (f) Oka, T.; Murai, A. Tetrahedron 1998, 54, 1-20.
9. (g) Oka, T.; Fujiwara, K.; Murai, A. Tetrahedron 1998, 54, 21-44.
10. Kirschbaum, B.; Isobe, M. unpublished results.
11. This anti stereochemistry was temporarily assigned from the chemical shift of the sp carbon with '*' at 80.5 ppm (Scheme I). The details of the NMR empirical rule will be discussed in the Table.
12. Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1992, 33, 7911-7914.
13. 4 and concentrated. The crude product was purified by silica gel chromatography to afford 5b (223 mg, 82%) as a single diastereoisomer.
14. (a) Isobe, M.; Nishizawa, R.; Nishikawa, T.; Yoza, K. Tetrahedron Lett. 1999, 40, 6927-6932.
15. (b) Isobe, M.; Jiang, Y. Tetrahedron Lett. 1995, 36, 567-570.
16. Liu, T.-Z.; Isobe, M. Synlett 2000, 2, 266-268.
17. Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978.
18. 7 (M+H): 529.3087; found: 529.3076.