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Volumn 56, Issue 30, 2000, Pages 5391-5404

Synthetic studies on the HIJK-ring fragment of ciguatoxin

Author keywords

Acetylene biscobalthexacarbonyl; Ciguatoxin; Cyclization; Heteroconjugate addition; Sonogashira coupling

Indexed keywords

ACETYLENE DERIVATIVE; ALKENE DERIVATIVE; CARBOHYDRATE DERIVATIVE; CIGUATOXIN; COBALT COMPLEX; IODINE DERIVATIVE; VINYL DERIVATIVE;

EID: 0034698153     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00467-1     Document Type: Article
Times cited : (41)

References (54)
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    • For recent synthetic studies from other groups, see: (a)
    • For recent synthetic studies from other groups, see: (a) Sasaki, M.; Noguchi, T.; Tachibana, K. Tetrahedron Lett. 1999, 40, 1337-1340. (b) Sasaki, M.; Fuwa, H.; Ishikawa, M.; Tachibana, K. Org. Lett. 1999, 1, 1075-1077. (c) Sasaki, M.; Noguchi, T.; Fuwa, H.; Tachibana, K. Tetrahedron Lett. 2000, 41, 1425-1428. (d) Oguri, H.; Sakaki, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1999, 40, 5405-5408. (e) Maeda, K.; Oishi, T.; Oguri, H.; Hirama, M. Chem. Commun. 1999, 1063-1064. (f) Oishi, T.; Nagumo, Y.; Shoji, M.; Brazidec, J.-Y. L.; Uehara, H.; Hirama, M. Chem. Commun. 1999, 2035-2036. (g) Oka, T.; Murai, A. Tetrahedron 1998, 54, 1-20. (h) Oka, T.; Fujiwara, K.; Murai, A. Tetrahedron 1998, 54, 21-44.
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    • For recent synthetic studies from other groups, see: (a) Sasaki, M.; Noguchi, T.; Tachibana, K. Tetrahedron Lett. 1999, 40, 1337-1340. (b) Sasaki, M.; Fuwa, H.; Ishikawa, M.; Tachibana, K. Org. Lett. 1999, 1, 1075-1077. (c) Sasaki, M.; Noguchi, T.; Fuwa, H.; Tachibana, K. Tetrahedron Lett. 2000, 41, 1425-1428. (d) Oguri, H.; Sakaki, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1999, 40, 5405-5408. (e) Maeda, K.; Oishi, T.; Oguri, H.; Hirama, M. Chem. Commun. 1999, 1063-1064. (f) Oishi, T.; Nagumo, Y.; Shoji, M.; Brazidec, J.-Y. L.; Uehara, H.; Hirama, M. Chem. Commun. 1999, 2035-2036. (g) Oka, T.; Murai, A. Tetrahedron 1998, 54, 1-20. (h) Oka, T.; Fujiwara, K.; Murai, A. Tetrahedron 1998, 54, 21-44.
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    • (d)
    • For recent synthetic studies from other groups, see: (a) Sasaki, M.; Noguchi, T.; Tachibana, K. Tetrahedron Lett. 1999, 40, 1337-1340. (b) Sasaki, M.; Fuwa, H.; Ishikawa, M.; Tachibana, K. Org. Lett. 1999, 1, 1075-1077. (c) Sasaki, M.; Noguchi, T.; Fuwa, H.; Tachibana, K. Tetrahedron Lett. 2000, 41, 1425-1428. (d) Oguri, H.; Sakaki, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1999, 40, 5405-5408. (e) Maeda, K.; Oishi, T.; Oguri, H.; Hirama, M. Chem. Commun. 1999, 1063-1064. (f) Oishi, T.; Nagumo, Y.; Shoji, M.; Brazidec, J.-Y. L.; Uehara, H.; Hirama, M. Chem. Commun. 1999, 2035-2036. (g) Oka, T.; Murai, A. Tetrahedron 1998, 54, 1-20. (h) Oka, T.; Fujiwara, K.; Murai, A. Tetrahedron 1998, 54, 21-44.
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    • For recent synthetic studies from other groups, see: (a) Sasaki, M.; Noguchi, T.; Tachibana, K. Tetrahedron Lett. 1999, 40, 1337-1340. (b) Sasaki, M.; Fuwa, H.; Ishikawa, M.; Tachibana, K. Org. Lett. 1999, 1, 1075-1077. (c) Sasaki, M.; Noguchi, T.; Fuwa, H.; Tachibana, K. Tetrahedron Lett. 2000, 41, 1425-1428. (d) Oguri, H.; Sakaki, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1999, 40, 5405-5408. (e) Maeda, K.; Oishi, T.; Oguri, H.; Hirama, M. Chem. Commun. 1999, 1063-1064. (f) Oishi, T.; Nagumo, Y.; Shoji, M.; Brazidec, J.-Y. L.; Uehara, H.; Hirama, M. Chem. Commun. 1999, 2035-2036. (g) Oka, T.; Murai, A. Tetrahedron 1998, 54, 1-20. (h) Oka, T.; Fujiwara, K.; Murai, A. Tetrahedron 1998, 54, 21-44.
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    • For recent synthetic studies from other groups, see: (a) Sasaki, M.; Noguchi, T.; Tachibana, K. Tetrahedron Lett. 1999, 40, 1337-1340. (b) Sasaki, M.; Fuwa, H.; Ishikawa, M.; Tachibana, K. Org. Lett. 1999, 1, 1075-1077. (c) Sasaki, M.; Noguchi, T.; Fuwa, H.; Tachibana, K. Tetrahedron Lett. 2000, 41, 1425-1428. (d) Oguri, H.; Sakaki, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1999, 40, 5405-5408. (e) Maeda, K.; Oishi, T.; Oguri, H.; Hirama, M. Chem. Commun. 1999, 1063-1064. (f) Oishi, T.; Nagumo, Y.; Shoji, M.; Brazidec, J.-Y. L.; Uehara, H.; Hirama, M. Chem. Commun. 1999, 2035-2036. (g) Oka, T.; Murai, A. Tetrahedron 1998, 54, 1-20. (h) Oka, T.; Fujiwara, K.; Murai, A. Tetrahedron 1998, 54, 21-44.
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    • (g)
    • For recent synthetic studies from other groups, see: (a) Sasaki, M.; Noguchi, T.; Tachibana, K. Tetrahedron Lett. 1999, 40, 1337-1340. (b) Sasaki, M.; Fuwa, H.; Ishikawa, M.; Tachibana, K. Org. Lett. 1999, 1, 1075-1077. (c) Sasaki, M.; Noguchi, T.; Fuwa, H.; Tachibana, K. Tetrahedron Lett. 2000, 41, 1425-1428. (d) Oguri, H.; Sakaki, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1999, 40, 5405-5408. (e) Maeda, K.; Oishi, T.; Oguri, H.; Hirama, M. Chem. Commun. 1999, 1063-1064. (f) Oishi, T.; Nagumo, Y.; Shoji, M.; Brazidec, J.-Y. L.; Uehara, H.; Hirama, M. Chem. Commun. 1999, 2035-2036. (g) Oka, T.; Murai, A. Tetrahedron 1998, 54, 1-20. (h) Oka, T.; Fujiwara, K.; Murai, A. Tetrahedron 1998, 54, 21-44.
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    • (h)
    • For recent synthetic studies from other groups, see: (a) Sasaki, M.; Noguchi, T.; Tachibana, K. Tetrahedron Lett. 1999, 40, 1337-1340. (b) Sasaki, M.; Fuwa, H.; Ishikawa, M.; Tachibana, K. Org. Lett. 1999, 1, 1075-1077. (c) Sasaki, M.; Noguchi, T.; Fuwa, H.; Tachibana, K. Tetrahedron Lett. 2000, 41, 1425-1428. (d) Oguri, H.; Sakaki, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1999, 40, 5405-5408. (e) Maeda, K.; Oishi, T.; Oguri, H.; Hirama, M. Chem. Commun. 1999, 1063-1064. (f) Oishi, T.; Nagumo, Y.; Shoji, M.; Brazidec, J.-Y. L.; Uehara, H.; Hirama, M. Chem. Commun. 1999, 2035-2036. (g) Oka, T.; Murai, A. Tetrahedron 1998, 54, 1-20. (h) Oka, T.; Fujiwara, K.; Murai, A. Tetrahedron 1998, 54, 21-44.
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    • 2, 100%
    • 2, 100%.
  • 52
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    • 2, 85%; (c) NaH, BnBr, DMF, 0°C, 89%
    • 2, 85%; (c) NaH, BnBr, DMF, 0°C, 89%.
  • 53
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    • (a) See ref. 10(c). (b) (c) See ref. 10(b)
    • (a) See ref. 10(c). (b) Hosokawa, S.; Isobe, M. Tetrahedron Lett. 1998, 39, 2609-2612. (c) See ref. 10(b).
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    • Hosokawa, S.1    Isobe, M.2


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