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Volumn 38, Issue 1, 1997, Pages 123-126

Synthesis of brevetoxin sub-units by sequential ring-closing metathesis and hydroboration

Author keywords

[No Author keywords available]

Indexed keywords

BREVETOXIN;

EID: 0031031774     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02232-0     Document Type: Article
Times cited : (150)

References (35)
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    • For some examples of methods developed for the synthesis of polycyclic ether frameworks, see: Nicolaou, K. C.; Hwang, C.-K.; Nugiel, D. A. J. Am. Chem. Soc., 1989, 111, 4136; Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. ibid., 1989, 111, 5330; Nicolaou, K. C.; Hwang, C.-K.; Marron, B. E.; DeFrees, S. A.; Couladouros, E. A.; Abe, Y.; Carroll, P. J.; Snyder, J. P. ibid., 1990, 112, 3040; Zárraga, M.; Martín, J. D. Tetrahedron Lett., 1991, 32, 2249. Yamamoto, Y.; Yamada, J.; Kadota, I. ibid., 1991, 32, 7069.
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    • For some examples of methods developed for the synthesis of polycyclic ether frameworks, see: Nicolaou, K. C.; Hwang, C.-K.; Nugiel, D. A. J. Am. Chem. Soc., 1989, 111, 4136; Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. ibid., 1989, 111, 5330; Nicolaou, K. C.; Hwang, C.-K.; Marron, B. E.; DeFrees, S. A.; Couladouros, E. A.; Abe, Y.; Carroll, P. J.; Snyder, J. P. ibid., 1990, 112, 3040; Zárraga, M.; Martín, J. D. Tetrahedron Lett., 1991, 32, 2249. Yamamoto, Y.; Yamada, J.; Kadota, I. ibid., 1991, 32, 7069.
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    • For examples of the hydroboration of related cyclic enol ethers, see: Nicolaou, K. C.; McGarry, D. G.; Sommers, P. K. J. Am. Chem. Soc., 1990, 112, 3696; Alvarez, E.; Rico, M.; Rodríguez, R. M.; Zurita, D.; Martín, J. D. Tetrahedron Lett., 1992. 33, 3385; Fei, F.; Murai, A. Synlett, 1995, 863.
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    • For examples of the hydroboration of related cyclic enol ethers, see: Nicolaou, K. C.; McGarry, D. G.; Sommers, P. K. J. Am. Chem. Soc., 1990, 112, 3696; Alvarez, E.; Rico, M.; Rodríguez, R. M.; Zurita, D.; Martín, J. D. Tetrahedron Lett., 1992. 33, 3385; Fei, F.; Murai, A. Synlett, 1995, 863.
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    • For examples of the hydroboration of related cyclic enol ethers, see: Nicolaou, K. C.; McGarry, D. G.; Sommers, P. K. J. Am. Chem. Soc., 1990, 112, 3696; Alvarez, E.; Rico, M.; Rodríguez, R. M.; Zurita, D.; Martín, J. D. Tetrahedron Lett., 1992. 33, 3385; Fei, F.; Murai, A. Synlett, 1995, 863.
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    • The catalyst (1) used in these studies was purchased from Strem Chemicals (U.K.)
    • The catalyst (1) used in these studies was purchased from Strem Chemicals (U.K.).
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    • It is known that Lewis acids (including alkyl boranes) promote elimination of the intermediate organoboranes during the hydroboration of enol ethers: Pasto D. J.; Cumbo, C. C. J. Am. Chem. Soc., 1964, 86, 4343.
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    • The enol ether 4d was not produced by isomerisation and ring-opening of the cyclo-dimer 9, since compound 4d was not formed upon re-exposure of the cyclo-dimer to the catalyst 1
    • The enol ether 4d was not produced by isomerisation and ring-opening of the cyclo-dimer 9, since compound 4d was not formed upon re-exposure of the cyclo-dimer to the catalyst 1.


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