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Volumn 59, Issue 35, 2003, Pages 6851-6872

Synthesis of the JKLM-ring fragment of ciguatoxin

Author keywords

Ciguatoxin; Lactone; Spiroketalization

Indexed keywords

ACETYLENE; CIGUATOXIN; COBALT COMPLEX; ETHER DERIVATIVE;

EID: 0043160327     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00873-1     Document Type: Article
Times cited : (52)

References (91)
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    • For construction of medium sized ether rings via actylene cobalt complexes in a highly stereoselective syn-trans orientation, see: (a) Isobe M., Yenjai C., Tanaka S. Synlett. 11:1994;916-918 (b) Yenjai C., Isobe M. Tetrahedron. 54:1998;2509-2520 (c) Isobe M., Hosokawa S., Kira K. Chem. Lett. 1996;473-474. (d) For a review, see Isobe M., Nishizawa R., Hosokawa S., Nishikawa T. Chem. Commun. 1998;2665-2676. For reductive decomplexation reaction into cis-olefins or vinylsilanes, see: (e) Hosokawa S., Isobe M. Tetrahedron Lett. 39:1998;2609-2612 (f) Shibuya S., Isobe M. Tetrahedron. 54:1998;6677-6698 (g) Takai S., Ploypradith P., Hamajima A., Kira K., Isobe M. Synlett. 2002;588-592. For ring-opening reactions of cyclic α,β-epoxysilanes into allyl alcohols, see: (h) Kira K., Isobe M. Chem. Lett. 2001;432-433 (i) Kira K., Hamajima A., Isobe M. Tetrahedron. 58:2002;1875-1888. For stereoselective heteroconjugate additions, see: (j) Isobe M., Kitamura M., Goto T. Tetrahedron Lett. 20:1979;3465-3468 (k) Isobe M., Funabashi Y., Ichikawa Y., Mio S., Goto T. Tetrahedron Lett. 25:1984;2021-2024 (l) Isobe M. New Synthetic Methods Using Vinyl Sulfones - Developments in Heteroconjugate Addition. Zwanenburg B., Klunder A.J.H. Studies in Organic Chemistry. Studies in Organic Chemistry. Vol. 28:1987;209-229.
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    • For construction of medium sized ether rings via actylene cobalt complexes in a highly stereoselective syn-trans orientation, see: (a) Isobe M., Yenjai C., Tanaka S. Synlett. 11:1994;916-918 (b) Yenjai C., Isobe M. Tetrahedron. 54:1998;2509-2520 (c) Isobe M., Hosokawa S., Kira K. Chem. Lett. 1996;473-474. (d) For a review, see Isobe M., Nishizawa R., Hosokawa S., Nishikawa T. Chem. Commun. 1998;2665-2676. For reductive decomplexation reaction into cis-olefins or vinylsilanes, see: (e) Hosokawa S., Isobe M. Tetrahedron Lett. 39:1998;2609-2612 (f) Shibuya S., Isobe M. Tetrahedron. 54:1998;6677-6698 (g) Takai S., Ploypradith P., Hamajima A., Kira K., Isobe M. Synlett. 2002;588-592. For ring-opening reactions of cyclic α,β-epoxysilanes into allyl alcohols, see: (h) Kira K., Isobe M. Chem. Lett. 2001;432-433 (i) Kira K., Hamajima A., Isobe M. Tetrahedron. 58:2002;1875-1888. For stereoselective heteroconjugate additions, see: (j) Isobe M., Kitamura M., Goto T. Tetrahedron Lett. 20:1979;3465-3468 (k) Isobe M., Funabashi Y., Ichikawa Y., Mio S., Goto T. Tetrahedron Lett. 25:1984;2021-2024 (l) Isobe M. New Synthetic Methods Using Vinyl Sulfones - Developments in Heteroconjugate Addition. Zwanenburg B., Klunder A.J.H. Studies in Organic Chemistry. Studies in Organic Chemistry. Vol. 28:1987;209-229.
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    • For construction of medium sized ether rings via actylene cobalt complexes in a highly stereoselective syn-trans orientation, see: (a) Isobe M., Yenjai C., Tanaka S. Synlett. 11:1994;916-918 (b) Yenjai C., Isobe M. Tetrahedron. 54:1998;2509-2520 (c) Isobe M., Hosokawa S., Kira K. Chem. Lett. 1996;473-474. (d) For a review, see Isobe M., Nishizawa R., Hosokawa S., Nishikawa T. Chem. Commun. 1998;2665-2676. For reductive decomplexation reaction into cis-olefins or vinylsilanes, see: (e) Hosokawa S., Isobe M. Tetrahedron Lett. 39:1998;2609-2612 (f) Shibuya S., Isobe M. Tetrahedron. 54:1998;6677-6698 (g) Takai S., Ploypradith P., Hamajima A., Kira K., Isobe M. Synlett. 2002;588-592. For ring-opening reactions of cyclic α,β-epoxysilanes into allyl alcohols, see: (h) Kira K., Isobe M. Chem. Lett. 2001;432-433 (i) Kira K., Hamajima A., Isobe M. Tetrahedron. 58:2002;1875-1888. For stereoselective heteroconjugate additions, see: (j) Isobe M., Kitamura M., Goto T. Tetrahedron Lett. 20:1979;3465-3468 (k) Isobe M., Funabashi Y., Ichikawa Y., Mio S., Goto T. Tetrahedron Lett. 25:1984;2021-2024 (l) Isobe M. New Synthetic Methods Using Vinyl Sulfones - Developments in Heteroconjugate Addition. Zwanenburg B., Klunder A.J.H. Studies in Organic Chemistry. Studies in Organic Chemistry. Vol. 28:1987;209-229.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 2609-2612
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    • For construction of medium sized ether rings via actylene cobalt complexes in a highly stereoselective syn-trans orientation, see: (a) Isobe M., Yenjai C., Tanaka S. Synlett. 11:1994;916-918 (b) Yenjai C., Isobe M. Tetrahedron. 54:1998;2509-2520 (c) Isobe M., Hosokawa S., Kira K. Chem. Lett. 1996;473-474. (d) For a review, see Isobe M., Nishizawa R., Hosokawa S., Nishikawa T. Chem. Commun. 1998;2665-2676. For reductive decomplexation reaction into cis-olefins or vinylsilanes, see: (e) Hosokawa S., Isobe M. Tetrahedron Lett. 39:1998;2609-2612 (f) Shibuya S., Isobe M. Tetrahedron. 54:1998;6677-6698 (g) Takai S., Ploypradith P., Hamajima A., Kira K., Isobe M. Synlett. 2002;588-592. For ring-opening reactions of cyclic α,β-epoxysilanes into allyl alcohols, see: (h) Kira K., Isobe M. Chem. Lett. 2001;432-433 (i) Kira K., Hamajima A., Isobe M. Tetrahedron. 58:2002;1875-1888. For stereoselective heteroconjugate additions, see: (j) Isobe M., Kitamura M., Goto T. Tetrahedron Lett. 20:1979;3465-3468 (k) Isobe M., Funabashi Y., Ichikawa Y., Mio S., Goto T. Tetrahedron Lett. 25:1984;2021-2024 (l) Isobe M. New Synthetic Methods Using Vinyl Sulfones - Developments in Heteroconjugate Addition. Zwanenburg B., Klunder A.J.H. Studies in Organic Chemistry. Studies in Organic Chemistry. Vol. 28:1987;209-229.
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    • For construction of medium sized ether rings via actylene cobalt complexes in a highly stereoselective syn-trans orientation, see: (a) Isobe M., Yenjai C., Tanaka S. Synlett. 11:1994;916-918 (b) Yenjai C., Isobe M. Tetrahedron. 54:1998;2509-2520 (c) Isobe M., Hosokawa S., Kira K. Chem. Lett. 1996;473-474. (d) For a review, see Isobe M., Nishizawa R., Hosokawa S., Nishikawa T. Chem. Commun. 1998;2665-2676. For reductive decomplexation reaction into cis-olefins or vinylsilanes, see: (e) Hosokawa S., Isobe M. Tetrahedron Lett. 39:1998;2609-2612 (f) Shibuya S., Isobe M. Tetrahedron. 54:1998;6677-6698 (g) Takai S., Ploypradith P., Hamajima A., Kira K., Isobe M. Synlett. 2002;588-592. For ring-opening reactions of cyclic α,β-epoxysilanes into allyl alcohols, see: (h) Kira K., Isobe M. Chem. Lett. 2001;432-433 (i) Kira K., Hamajima A., Isobe M. Tetrahedron. 58:2002;1875-1888. For stereoselective heteroconjugate additions, see: (j) Isobe M., Kitamura M., Goto T. Tetrahedron Lett. 20:1979;3465-3468 (k) Isobe M., Funabashi Y., Ichikawa Y., Mio S., Goto T. Tetrahedron Lett. 25:1984;2021-2024 (l) Isobe M. New Synthetic Methods Using Vinyl Sulfones - Developments in Heteroconjugate Addition. Zwanenburg B., Klunder A.J.H. Studies in Organic Chemistry. Studies in Organic Chemistry. Vol. 28:1987;209-229.
    • (2002) Synlett , pp. 588-592
    • Takai, S.1    Ploypradith, P.2    Hamajima, A.3    Kira, K.4    Isobe, M.5
  • 36
    • 0035533864 scopus 로고    scopus 로고
    • For construction of medium sized ether rings via actylene cobalt complexes in a highly stereoselective syn-trans orientation, see: (a) Isobe M., Yenjai C., Tanaka S. Synlett. 11:1994;916-918 (b) Yenjai C., Isobe M. Tetrahedron. 54:1998;2509-2520 (c) Isobe M., Hosokawa S., Kira K. Chem. Lett. 1996;473-474. (d) For a review, see Isobe M., Nishizawa R., Hosokawa S., Nishikawa T. Chem. Commun. 1998;2665-2676. For reductive decomplexation reaction into cis-olefins or vinylsilanes, see: (e) Hosokawa S., Isobe M. Tetrahedron Lett. 39:1998;2609-2612 (f) Shibuya S., Isobe M. Tetrahedron. 54:1998;6677-6698 (g) Takai S., Ploypradith P., Hamajima A., Kira K., Isobe M. Synlett. 2002;588-592. For ring-opening reactions of cyclic α,β-epoxysilanes into allyl alcohols, see: (h) Kira K., Isobe M. Chem. Lett. 2001;432-433 (i) Kira K., Hamajima A., Isobe M. Tetrahedron. 58:2002;1875-1888. For stereoselective heteroconjugate additions, see: (j) Isobe M., Kitamura M., Goto T. Tetrahedron Lett. 20:1979;3465-3468 (k) Isobe M., Funabashi Y., Ichikawa Y., Mio S., Goto T. Tetrahedron Lett. 25:1984;2021-2024 (l) Isobe M. New Synthetic Methods Using Vinyl Sulfones - Developments in Heteroconjugate Addition. Zwanenburg B., Klunder A.J.H. Studies in Organic Chemistry. Studies in Organic Chemistry. Vol. 28:1987;209-229.
    • (2001) Chem. Lett. , pp. 432-433
    • Kira, K.1    Isobe, M.2
  • 37
    • 0037017757 scopus 로고    scopus 로고
    • For construction of medium sized ether rings via actylene cobalt complexes in a highly stereoselective syn-trans orientation, see: (a) Isobe M., Yenjai C., Tanaka S. Synlett. 11:1994;916-918 (b) Yenjai C., Isobe M. Tetrahedron. 54:1998;2509-2520 (c) Isobe M., Hosokawa S., Kira K. Chem. Lett. 1996;473-474. (d) For a review, see Isobe M., Nishizawa R., Hosokawa S., Nishikawa T. Chem. Commun. 1998;2665-2676. For reductive decomplexation reaction into cis-olefins or vinylsilanes, see: (e) Hosokawa S., Isobe M. Tetrahedron Lett. 39:1998;2609-2612 (f) Shibuya S., Isobe M. Tetrahedron. 54:1998;6677-6698 (g) Takai S., Ploypradith P., Hamajima A., Kira K., Isobe M. Synlett. 2002;588-592. For ring-opening reactions of cyclic α,β-epoxysilanes into allyl alcohols, see: (h) Kira K., Isobe M. Chem. Lett. 2001;432-433 (i) Kira K., Hamajima A., Isobe M. Tetrahedron. 58:2002;1875-1888. For stereoselective heteroconjugate additions, see: (j) Isobe M., Kitamura M., Goto T. Tetrahedron Lett. 20:1979;3465-3468 (k) Isobe M., Funabashi Y., Ichikawa Y., Mio S., Goto T. Tetrahedron Lett. 25:1984;2021-2024 (l) Isobe M. New Synthetic Methods Using Vinyl Sulfones - Developments in Heteroconjugate Addition. Zwanenburg B., Klunder A.J.H. Studies in Organic Chemistry. Studies in Organic Chemistry. Vol. 28:1987;209-229.
    • (2002) Tetrahedron , vol.58 , pp. 1875-1888
    • Kira, K.1    Hamajima, A.2    Isobe, M.3
  • 38
    • 0002845351 scopus 로고
    • For construction of medium sized ether rings via actylene cobalt complexes in a highly stereoselective syn-trans orientation, see: (a) Isobe M., Yenjai C., Tanaka S. Synlett. 11:1994;916-918 (b) Yenjai C., Isobe M. Tetrahedron. 54:1998;2509-2520 (c) Isobe M., Hosokawa S., Kira K. Chem. Lett. 1996;473-474. (d) For a review, see Isobe M., Nishizawa R., Hosokawa S., Nishikawa T. Chem. Commun. 1998;2665-2676. For reductive decomplexation reaction into cis-olefins or vinylsilanes, see: (e) Hosokawa S., Isobe M. Tetrahedron Lett. 39:1998;2609-2612 (f) Shibuya S., Isobe M. Tetrahedron. 54:1998;6677-6698 (g) Takai S., Ploypradith P., Hamajima A., Kira K., Isobe M. Synlett. 2002;588-592. For ring-opening reactions of cyclic α,β-epoxysilanes into allyl alcohols, see: (h) Kira K., Isobe M. Chem. Lett. 2001;432-433 (i) Kira K., Hamajima A., Isobe M. Tetrahedron. 58:2002;1875-1888. For stereoselective heteroconjugate additions, see: (j) Isobe M., Kitamura M., Goto T. Tetrahedron Lett. 20:1979;3465-3468 (k) Isobe M., Funabashi Y., Ichikawa Y., Mio S., Goto T. Tetrahedron Lett. 25:1984;2021-2024 (l) Isobe M. New Synthetic Methods Using Vinyl Sulfones - Developments in Heteroconjugate Addition. Zwanenburg B., Klunder A.J.H. Studies in Organic Chemistry. Studies in Organic Chemistry. Vol. 28:1987;209-229.
    • (1979) Tetrahedron Lett. , vol.20 , pp. 3465-3468
    • Isobe, M.1    Kitamura, M.2    Goto, T.3
  • 39
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    • For construction of medium sized ether rings via actylene cobalt complexes in a highly stereoselective syn-trans orientation, see: (a) Isobe M., Yenjai C., Tanaka S. Synlett. 11:1994;916-918 (b) Yenjai C., Isobe M. Tetrahedron. 54:1998;2509-2520 (c) Isobe M., Hosokawa S., Kira K. Chem. Lett. 1996;473-474. (d) For a review, see Isobe M., Nishizawa R., Hosokawa S., Nishikawa T. Chem. Commun. 1998;2665-2676. For reductive decomplexation reaction into cis-olefins or vinylsilanes, see: (e) Hosokawa S., Isobe M. Tetrahedron Lett. 39:1998;2609-2612 (f) Shibuya S., Isobe M. Tetrahedron. 54:1998;6677-6698 (g) Takai S., Ploypradith P., Hamajima A., Kira K., Isobe M. Synlett. 2002;588-592. For ring-opening reactions of cyclic α,β-epoxysilanes into allyl alcohols, see: (h) Kira K., Isobe M. Chem. Lett. 2001;432-433 (i) Kira K., Hamajima A., Isobe M. Tetrahedron. 58:2002;1875-1888. For stereoselective heteroconjugate additions, see: (j) Isobe M., Kitamura M., Goto T. Tetrahedron Lett. 20:1979;3465-3468 (k) Isobe M., Funabashi Y., Ichikawa Y., Mio S., Goto T. Tetrahedron Lett. 25:1984;2021-2024 (l) Isobe M. New Synthetic Methods Using Vinyl Sulfones - Developments in Heteroconjugate Addition. Zwanenburg B., Klunder A.J.H. Studies in Organic Chemistry. Studies in Organic Chemistry. Vol. 28:1987;209-229.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 2021-2024
    • Isobe, M.1    Funabashi, Y.2    Ichikawa, Y.3    Mio, S.4    Goto, T.5
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    • For construction of medium sized ether rings via actylene cobalt complexes in a highly stereoselective syn-trans orientation, see: (a) Isobe M., Yenjai C., Tanaka S. Synlett. 11:1994;916-918 (b) Yenjai C., Isobe M. Tetrahedron. 54:1998;2509-2520 (c) Isobe M., Hosokawa S., Kira K. Chem. Lett. 1996;473-474. (d) For a review, see Isobe M., Nishizawa R., Hosokawa S., Nishikawa T. Chem. Commun. 1998;2665-2676. For reductive decomplexation reaction into cis-olefins or vinylsilanes, see: (e) Hosokawa S., Isobe M. Tetrahedron Lett. 39:1998;2609-2612 (f) Shibuya S., Isobe M. Tetrahedron. 54:1998;6677-6698 (g) Takai S., Ploypradith P., Hamajima A., Kira K., Isobe M. Synlett. 2002;588-592. For ring-opening reactions of cyclic α,β-epoxysilanes into allyl alcohols, see: (h) Kira K., Isobe M. Chem. Lett. 2001;432-433 (i) Kira K., Hamajima A., Isobe M. Tetrahedron. 58:2002;1875-1888. For stereoselective heteroconjugate additions, see: (j) Isobe M., Kitamura M., Goto T. Tetrahedron Lett. 20:1979;3465-3468 (k) Isobe M., Funabashi Y., Ichikawa Y., Mio S., Goto T. Tetrahedron Lett. 25:1984;2021-2024 (l) Isobe M. New Synthetic Methods Using Vinyl Sulfones - Developments in Heteroconjugate Addition. Zwanenburg B., Klunder A.J.H. Studies in Organic Chemistry. Studies in Organic Chemistry. Vol. 28:1987;209-229.
    • (1987) Studies in Organic Chemistry , vol.28 , pp. 209-229
    • Isobe, M.1
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    • For other syntheses of enlacton, see: (a) Valverde S., Herradon B., Martin-Lomas M. Tetrahedron Lett. 26:1985;3731-3734 (b) Chmielewski M., Jurczak J., Maciejewski S. Carbohydr. Res. 165:1987;111-115.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 3731-3734
    • Valverde, S.1    Herradon, B.2    Martin-Lomas, M.3
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    • For other syntheses of enlacton, see: (a) Valverde S., Herradon B., Martin-Lomas M. Tetrahedron Lett. 26:1985;3731-3734 (b) Chmielewski M., Jurczak J., Maciejewski S. Carbohydr. Res. 165:1987;111-115.
    • (1987) Carbohydr. Res. , vol.165 , pp. 111-115
    • Chmielewski, M.1    Jurczak, J.2    Maciejewski, S.3


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