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Volumn 8, Issue 19, 2002, Pages 4346-4353

New efficient iterative approaches to polycyclic ethers

Author keywords

Cyclization; Fused ring systems; Iterative synthesis; Natural products; Polyethers

Indexed keywords

ITERATIVE METHODS; SUBSTITUTION REACTIONS; TOXIC MATERIALS;

EID: 0037020310     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20021004)8:19<4346::AID-CHEM4346>3.0.CO;2-S     Document Type: Article
Times cited : (72)

References (52)
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    • Y. Mori, K. Yaegeshi, H. Furukawa, J. Am. Chem. Soc. 1997, 119, 4557-4558, 36 steps from tri-O-acetyl-D-glucal to a Yamamoto intermediate, 43 steps overall. For comparison, Nicolaou group: 54 steps from D-mannose. K. C. Nicolaou, K. R. Reddy, G. Skokotas, F. Sato, X.-Y. Xiao, C.-K. Hwang, J. Am. Chem. Soc. 1993, 115, 3558-3575; Nakata group, 61 steps from geranyl acetate, M. Morimoto, H. Matsukura, T. Nakata, Tetrahedron Lett. 1996, 37, 6365-6368; Yamamoto group, 52 steps from D-mannose, I. Kadota, Y. Yamamoto, J. Org. Chem. 1998, 63, 6591-6606.
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    • note
    • This comparison is not quite accurate; the Mori synthesis is asymmetric and requires nine steps for the conversion of tri-O- acetyl-D-glucal to their A-ring surrogate, see ref. [9]. The Rainier synthesis is racemic and requires five steps for their A-ring surrogate. However, the authors mention that the hetero-Diels-Alder reaction can be accomplished asymmetrically (ref. [18]).
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    • III catalyst. For Jacobsen's catalyst, see A. G. Dossetter, T. F. Jamison, E. N. Jacobsen, Angew. Chem. 1999, 111, 2549-2552; Angew. Chem. Int. Ed. 1999, 38, 2398-2400.
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    • see ref [26]
    • Compound 59 was synthesized from L-arabinose in seven steps, see ref. [26]. For the 6-endo cyclization of methyl epoxides, see G. Matsuo, H. Matsukura, N. Hori, T. Nakata, Tetrahedron Lett. 2000, 41, 7673-7684.
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    • Compound 59 was synthesized from L-arabinose in seven steps, see ref. [26]. For the 6-endo cyclization of methyl epoxides, see G. Matsuo, H. Matsukura, N. Hori, T. Nakata, Tetrahedron Lett. 2000, 41, 7673-7684.
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    • Matsuo, G.1    Matsukura, H.2    Hori, N.3    Nakata, T.4
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    • See also refs. [1a], [2], [3] and [5]
    • K. C. Nicolaou, M. E. Duggan, C.-K. Hwang, P. K. Somers, J. Chem. Soc. Chem. Commun. 1985,1359-1362. See also refs. [1a], [2], [3] and [5].
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    • 0032481078 scopus 로고    scopus 로고
    • For leading references for convergent polyether methods see a) M. Sasaki, H. Fuwa, M. Inoue, K. Tachibana, Tetrahedron Lett. 1998, 39, 9027-9030; b) M. Sasaki, H. Fuwa, M. Ishikawa, K. Tachibana, Org. Lett. 1999, 1, 1075-1077; (c) H. Fuwa, M. Sasaki, K. Tachibana, Org. Lett. 2001, 3, 3549-3552; d) K. Fujiwara, K. Saka, D. Takaoka, A. Murai, Synlett 1999, 1037-1040; e) Y. Mori, S. Mitsuoka, H. Furukawa, Tetrahedron Lett. 2000, 41, 4161-4164; f) Nicolaou used a convergent approach for the total syntheses of brevetoxin A and B, see refs. [2] and [3]; g) Hirama used a convergent approach for the total synthesis of ciguatoxin CTX3C (ref. [4]).
    • (1998) Tetrahedron Lett. , vol.39 , pp. 9027-9030
    • Sasaki, M.1    Fuwa, H.2    Inoue, M.3    Tachibana, K.4
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    • 0001016023 scopus 로고    scopus 로고
    • For leading references for convergent polyether methods see a) M. Sasaki, H. Fuwa, M. Inoue, K. Tachibana, Tetrahedron Lett. 1998, 39, 9027-9030; b) M. Sasaki, H. Fuwa, M. Ishikawa, K. Tachibana, Org. Lett. 1999, 1, 1075-1077; (c) H. Fuwa, M. Sasaki, K. Tachibana, Org. Lett. 2001, 3, 3549-3552; d) K. Fujiwara, K. Saka, D. Takaoka, A. Murai, Synlett 1999, 1037-1040; e) Y. Mori, S. Mitsuoka, H. Furukawa, Tetrahedron Lett. 2000, 41, 4161-4164; f) Nicolaou used a convergent approach for the total syntheses of brevetoxin A and B, see refs. [2] and [3]; g) Hirama used a convergent approach for the total synthesis of ciguatoxin CTX3C (ref. [4]).
    • (1999) Org. Lett. , vol.1 , pp. 1075-1077
    • Sasaki, M.1    Fuwa, H.2    Ishikawa, M.3    Tachibana, K.4
  • 48
    • 0035511917 scopus 로고    scopus 로고
    • For leading references for convergent polyether methods see a) M. Sasaki, H. Fuwa, M. Inoue, K. Tachibana, Tetrahedron Lett. 1998, 39, 9027-9030; b) M. Sasaki, H. Fuwa, M. Ishikawa, K. Tachibana, Org. Lett. 1999, 1, 1075-1077; (c) H. Fuwa, M. Sasaki, K. Tachibana, Org. Lett. 2001, 3, 3549-3552; d) K. Fujiwara, K. Saka, D. Takaoka, A. Murai, Synlett 1999, 1037-1040; e) Y. Mori, S. Mitsuoka, H. Furukawa, Tetrahedron Lett. 2000, 41, 4161-4164; f) Nicolaou used a convergent approach for the total syntheses of brevetoxin A and B, see refs. [2] and [3]; g) Hirama used a convergent approach for the total synthesis of ciguatoxin CTX3C (ref. [4]).
    • (2001) Org. Lett. , vol.3 , pp. 3549-3552
    • Fuwa, H.1    Sasaki, M.2    Tachibana, K.3
  • 49
    • 0032806956 scopus 로고    scopus 로고
    • For leading references for convergent polyether methods see a) M. Sasaki, H. Fuwa, M. Inoue, K. Tachibana, Tetrahedron Lett. 1998, 39, 9027-9030; b) M. Sasaki, H. Fuwa, M. Ishikawa, K. Tachibana, Org. Lett. 1999, 1, 1075-1077; (c) H. Fuwa, M. Sasaki, K. Tachibana, Org. Lett. 2001, 3, 3549-3552; d) K. Fujiwara, K. Saka, D. Takaoka, A. Murai, Synlett 1999, 1037-1040; e) Y. Mori, S. Mitsuoka, H. Furukawa, Tetrahedron Lett. 2000, 41, 4161-4164; f) Nicolaou used a convergent approach for the total syntheses of brevetoxin A and B, see refs. [2] and [3]; g) Hirama used a convergent approach for the total synthesis of ciguatoxin CTX3C (ref. [4]).
    • (1999) Synlett , pp. 1037-1040
    • Fujiwara, K.1    Saka, K.2    Takaoka, D.3    Murai, A.4
  • 50
    • 0034729520 scopus 로고    scopus 로고
    • For leading references for convergent polyether methods see a) M. Sasaki, H. Fuwa, M. Inoue, K. Tachibana, Tetrahedron Lett. 1998, 39, 9027-9030; b) M. Sasaki, H. Fuwa, M. Ishikawa, K. Tachibana, Org. Lett. 1999, 1, 1075-1077; (c) H. Fuwa, M. Sasaki, K. Tachibana, Org. Lett. 2001, 3, 3549-3552; d) K. Fujiwara, K. Saka, D. Takaoka, A. Murai, Synlett 1999, 1037-1040; e) Y. Mori, S. Mitsuoka, H. Furukawa, Tetrahedron Lett. 2000, 41, 4161-4164; f) Nicolaou used a convergent approach for the total syntheses of brevetoxin A and B, see refs. [2] and [3]; g) Hirama used a convergent approach for the total synthesis of ciguatoxin CTX3C (ref. [4]).
    • (2000) Tetrahedron Lett. , vol.41 , pp. 4161-4164
    • Mori, Y.1    Mitsuoka, S.2    Furukawa, H.3
  • 51
    • 0032481078 scopus 로고    scopus 로고
    • see refs. [2] and [3]
    • For leading references for convergent polyether methods see a) M. Sasaki, H. Fuwa, M. Inoue, K. Tachibana, Tetrahedron Lett. 1998, 39, 9027-9030; b) M. Sasaki, H. Fuwa, M. Ishikawa, K. Tachibana, Org. Lett. 1999, 1, 1075-1077; (c) H. Fuwa, M. Sasaki, K. Tachibana, Org. Lett. 2001, 3, 3549-3552; d) K. Fujiwara, K. Saka, D. Takaoka, A. Murai, Synlett 1999, 1037-1040; e) Y. Mori, S. Mitsuoka, H. Furukawa, Tetrahedron Lett. 2000, 41, 4161-4164; f) Nicolaou used a convergent approach for the total syntheses of brevetoxin A and B, see refs. [2] and [3]; g) Hirama used a convergent approach for the total synthesis of ciguatoxin CTX3C (ref. [4]).
  • 52
    • 0032481078 scopus 로고    scopus 로고
    • note
    • For leading references for convergent polyether methods see a) M. Sasaki, H. Fuwa, M. Inoue, K. Tachibana, Tetrahedron Lett. 1998, 39, 9027-9030; b) M. Sasaki, H. Fuwa, M. Ishikawa, K. Tachibana, Org. Lett. 1999, 1, 1075-1077; (c) H. Fuwa, M. Sasaki, K. Tachibana, Org. Lett. 2001, 3, 3549-3552; d) K. Fujiwara, K. Saka, D. Takaoka, A. Murai, Synlett 1999, 1037-1040; e) Y. Mori, S. Mitsuoka, H. Furukawa, Tetrahedron Lett. 2000, 41, 4161-4164; f) Nicolaou used a convergent approach for the total syntheses of brevetoxin A and B, see refs. [2] and [3]; g) Hirama used a convergent approach for the total synthesis of ciguatoxin CTX3C (ref. [4]).


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