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4
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0027144798
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c) G. R. Pettit, Z. A. Cichacz, C. L. Herald, F. Gao, M. R. Boyd, J. M. Schmidt, E. Hamel, R. Bai, J. Chem. Soc. Chem. Commun. 1994, 1605-1606.
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a) M. Kobayashi, S. Aoki, H. Sakai, K. Kawazoe, N. Kihara, T. Sasaki, I. Kitagawa, Tetrahedron Lett. 1993, 34, 2795-2798;
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b) M. Kobayashi, S. Aoki, H. Sakai, N. Kihara, T. Sasaki, I. Kitagawa. Chem. Pharm. Bull. 1993, 41, 989-991;
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Kobayashi, M.1
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12
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0029133540
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The spongistatins were shown to exhibit potent amimitotic activity resulting from strong tubulin binding: R. Bai, G. F. Taylor, Z. A. Cichacz, C. L. Herald, J. A. Kepler, G. R. Pettit, E. Hamel, Biochemistry 1995, 34, 9714-9721.
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Pettit, G.R.6
Hamel, E.7
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17
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0030733069
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e) L. Paterson, D. J. Wallace, K. R. Gibson, ibid. 1997, 38, 8911-8914;
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Paterson, L.1
Wallace, D.J.2
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20
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0030809932
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and references therein
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h) A. B. Smith, Q. Lin, K. Nakayama, A. M. Boldi, C. S. Brook, M. D. McBriar, W. H. Moser, M. Sobukawa, L. Zhuang, ibid. 1997, 38, 8675-8678, and references therein.
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Smith, A.B.1
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21
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0001289742
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D. A. Evans, B. W. Trotter, B. Côté, P. J. Coleman, L. C. Dias, A. N. Tyler, Angew. Chem. 1997, 109, 2957-2961; Angew. Chem. Int. Ed. Engl. 1997, 36, 2744-2747.
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Evans, D.A.1
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22
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0032491845
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D. A. Evans, B. W. Trotter, B. Côté, P. J. Coleman, L. C. Dias, A. N. Tyler, Angew. Chem. 1997, 109, 2957-2961; Angew. Chem. Int. Ed. Engl. 1997, 36, 2744-2747.
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23
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0346763735
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For this reason, we adopted the use of the name altohyrtin A in this paper. As discussed in the following paper, altohyrtin A is identical to spongistatin 1
-
For this reason, we adopted the use of the name altohyrtin A in this paper. As discussed in the following paper, altohyrtin A is identical to spongistatin 1.
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-
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24
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0026774529
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T. D. Aicher, K. R. Buszek, F. G. Fang, C. J. Forsyth, S. H. Jung, Y. Kishi, M. C. Matelich, P. M. Scola, D. M. Spero, S. K. Yoon, J. Am. Chem. Soc. 1992, 114, 3162-3164.
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Aicher, T.D.1
Buszek, K.R.2
Fang, F.G.3
Forsyth, C.J.4
Jung, S.H.5
Kishi, Y.6
Matelich, M.C.7
Scola, P.M.8
Spero, D.M.9
Yoon, S.K.10
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26
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33845375686
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a) H. Jin, J.-i. Uenishi, W. J. Christ, Y. Kishi, J. Am. Chem. Soc. 1986, 108, 5644-5646;
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Jin, H.1
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27
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0000959935
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b) K. Takai, M. Tagashira, T. Kuroda, K. Oshima, K. Utimoto, H. Nozaki, ibid. 1986, 108, 6048-6050;
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Takai, K.1
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28
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33751156806
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and references therein
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c) C. Chen, K. Tagami, Y. Kishi, J. Org. Chem. 1995, 60, 5386-5387, and references therein.
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Chen, C.1
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Kishi, Y.3
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29
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-
85087580643
-
-
13C NMR, MS, and others) were obtained for all new compounds
-
13C NMR, MS, and others) were obtained for all new compounds.
-
-
-
-
30
-
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0348024893
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-
note
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2O = para-toluenesulfonic anhydride.
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-
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32
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0027858856
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J. B. Nerenberg, D. T. Hung, P. K. Somers, S. L. Schreiber, J. Am. Chem. Soc. 1993, 115, 12621-12622.
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33
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0001553502
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Koerner, M.2
Parker, D.A.3
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35
-
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0346763733
-
-
note
-
Careful planning of the protecting group sequence allowed incorporation of an acetate on both the C5 and C15 alcohols (spongistatin 1) or only on the C5 alcohol (spongistatin 4). Protection of the C9 tertiary alcohol was also possible with silyl groups.
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-
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37
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0347394113
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The cis vinyl iodide corresponding to 26 might be suitable for the following key Michael cyclization, though this was not tested
-
The cis vinyl iodide corresponding to 26 might be suitable for the following key Michael cyclization, though this was not tested.
-
-
-
-
38
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0348024892
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-
note
-
The yields (50% to 80%) for the hydrolysis and subsequent Michael addition depended on the protecting group arrangement. A substrate bearing TBS groups on the C5, C9, and C15 alcohols and TBDPS on the C25 alcohol gave the best result. One of the by-products isolated in the case of 27 was the α,β-unsaturated ketone resulting from elimination of the C15 acetate.
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-
-
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39
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0346133241
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These experiments were performed by Dr. Yuan Wang at Eisai Research Institute, Andover, Massachusetts
-
These experiments were performed by Dr. Yuan Wang at Eisai Research Institute, Andover, Massachusetts.
-
-
-
-
40
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0346133240
-
-
note
-
For the C1 TBS ether of 28, distinct NOEs between the C19 and C21 protons and between the C27 and C22(eq) protons were observed. For the C1 TBS ether of 31, distinct NOEs between the C19 and C21 protons and between the C19 and C24(eq) protons were observed.
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-
-
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41
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0041807380
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a) W. P. Griffith, S. V. Ley, G. P. Whitcombe, A. D. White, J. Chem. Soc. Chem. Commun. 1987, 1625-1627;
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Griffith, W.P.1
Ley, S.V.2
Whitcombe, G.P.3
White, A.D.4
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42
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0027997412
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b) S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639-666.
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Ley, S.V.1
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Marsden, S.P.4
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44
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0348024891
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The Wittig reaction was also studied with the aldehyde bearing the unprotected carboxylic acid at C1; the olefination did yield the desired product but in much poorer yield
-
The Wittig reaction was also studied with the aldehyde bearing the unprotected carboxylic acid at C1; the olefination did yield the desired product but in much poorer yield.
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-
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45
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46149140781
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K. Horita, T. Yoshioka, T. Tanaka, Y. Oikawa, O. Yonemitsu, Tetrahedron 1986, 42, 3021-3028.
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Horita, K.1
Yoshioka, T.2
Tanaka, T.3
Oikawa, Y.4
Yonemitsu, O.5
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46
-
-
85087580920
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-
note
-
6]DMSO), whereas those in the C23 epimer were at δ= 5.80 and 5.37.
-
-
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48
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0022472782
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b) B. H. Lipshutz, H. Kotsuki, W. Lew, Tetrahedron Lett. 1986, 27, 4825-4828.
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54
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0001517035
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c) For a more convenient preparation of the DAMP reagent, see: D. G. Brown, E. J. Velthuisen, J. R. Commerford, R. G. Brisbois, T. R. Hoye, ibid. 1996, 61, 2540-2541.
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Brown, D.G.1
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0000588892
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Hara, S.1
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