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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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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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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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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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K. Takai, T. Kakiuchi, Y. Kataoka, K. Utimoto, J. Org. Chem. 1994, 59, 2668-2670.
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a) J. D. Rainier, S. P. Allwein, J. M. Cox, Org. Lett. 2000, 2, 231-234;
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b) J. D. Rainier, S. P. Allwein, J. M. Cox, J. Org. Chem, 2001, 66, 1380-1386.
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0035825039
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a) This reaction can also be accomplished with the 2nd generation Grubb's catalyst 37: J. D. Rainier, J. M. Cox, S. P. Allwein, Tetrahedron Lett. 2001, 42, 179-181;
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28
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0037017749
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b) for a recent full account of Rainier's iterative polycyclic ether methods, see S. P. Allwein, J. M. Cox, B. E. Howard, H. W. B. Johnson, J. D. Rainier, Tetrahedron 2002, 58, 1997-2009.
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2142833812
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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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32
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0000442967
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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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Dossetter, A.G.1
Jamison, T.F.2
Jacobsen, E.N.3
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33
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0033549737
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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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Angew. Chem. Int. Ed.
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34
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N. Hori, H. Matsukura, G. Matsuo, T. Nakata, Tetrahedron Lett. 1999, 40, 2811-2814.
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Hori, N.1
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0033544760
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a) G. Matsuo, N. Hori, T. Nakata, Tetrahedron Lett. 1999, 40, 8859-8862;
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b) N. Hori, H. Matsukura, T. Nakata, Org. Lett. 1999, 1, 1099-1101;
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Org. Lett.
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c) N. Hori, H. Matsukura, G. Matsuo, T. Nakata, Tetrahedron 2002, 58, 1853-1864.
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Tetrahedron
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Y. Sakamoto, G. Matsuo, H. Matsukura, T. Nakata, Org. Lett. 2001, 3, 2749-2752.
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39
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0034734601
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see ref [26]
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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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-
-
-
40
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0034734601
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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
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41
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37049103130
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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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37049103130
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See also refs. [1a], [2], [3] and [5]
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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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45
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F. P. Marmsäter, J. A. Vanecko, F. G. West, Tetrahedron 2002, 58, 2027-2040.
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Marmsäter, F.P.1
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West, F.G.3
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46
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0032481078
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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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Tetrahedron Lett.
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Sasaki, M.1
Fuwa, H.2
Inoue, M.3
Tachibana, K.4
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47
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0001016023
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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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(1999)
Org. Lett.
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Sasaki, M.1
Fuwa, H.2
Ishikawa, M.3
Tachibana, K.4
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48
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0035511917
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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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(2001)
Org. Lett.
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Fuwa, H.1
Sasaki, M.2
Tachibana, K.3
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49
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0032806956
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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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Synlett
, pp. 1037-1040
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Fujiwara, K.1
Saka, K.2
Takaoka, D.3
Murai, A.4
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50
-
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0034729520
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-
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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(2000)
Tetrahedron Lett.
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Mori, Y.1
Mitsuoka, S.2
Furukawa, H.3
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51
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0032481078
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-
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
-
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0032481078
-
-
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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-
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